High Purity Magnesium Oxide Market Size Report : Share, and Trends by Applications (Oriented Silicon Steel, Pharmaceutical Industry, Food Industry, Electrician Magnesium, Hydrotalcite, Rubber Industry, Chlorinated Polyethylene Cable, Others, Oriented Silicon Steel is the greatest segment of High Purity Magnesium Oxide application, with a share of 41% in .), By Types (Pharmaceutical Grade Magnesium Oxide, Food Grade Magnesium Oxide, Synthetic Magnesium Oxide, Synthetic Magnesium Oxide had the biggest market share of 85% in .), By Segmentation analysis, Regions and Forecast to . A fundamental analysis of market categories and subdivisions, including product types, applications, companies, and regions, is provided in this industry research analysis. It analyses the industry in depth, analyses historical data, projects the future, and facilitates in understanding the market circumstances, development potential, and impediments. The report provides a quantitative market analysis as well as information for establishing market expansion and accomplishment objectives.

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What is the High Purity Magnesium Oxide Market growth?

The High Purity Magnesium Oxide market is estimated to expand at an unexpected CAGR from to , reaching multimillion USD by compared to .

Examine the 144-page comprehensive TOC, tables, figures, and charts that offer unique facts, information, important statistics, trends, and competitive landscape details for this concentrated market.

The Global High Purity Magnesium Oxide Market is anticipated to rise at a considerable rate during the forecast period, between and . In , the market is growing at a steady rate and with the rising adoption of strategies by key players, the market is expected to rise over the projected horizon.

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Which are the leading players in the High Purity Magnesium Oxide market?

• JSC Kaustik
• ICL-IP
• Kyowa Chemical
• MAGNIFIN
• Buschle & Lepper S.A
• Lehmann&Voss&Co.
• Russian Mining Chemical
• Tateho Chemical
• Zehui Chemical
• UBE
• Konoshima Chemical
• Causmag International
• Qinghai Western Magnesium
• Martin Marietta Magnesia Specialties
• Grecian Magnesite
• Magnesia Mineral Compounds
• Celtic Chemicals Ltd

This research report is the result of an extensive primary and secondary research effort into the High Purity Magnesium Oxide market. It provides a thorough overview of the markets current and future objectives, along with a competitive analysis of the industry, broken down by application, type and regional trends. It also provides a dashboard overview of the past and present performance of leading companies. A variety of methodologies and analyses are used in the research to ensure accurate and comprehensive information about the High Purity Magnesium Oxide Market.

What Are the Different Types of High Purity Magnesium Oxide on the Market?

• Pharmaceutical Grade Magnesium Oxide
• Food Grade Magnesium Oxide
• Synthetic Magnesium Oxide
• Synthetic Magnesium Oxide had the biggest market share of 85% in .

Types help provide a comprehensive understanding of the diverse landscape within the High Purity Magnesium Oxide market. Keep in mind that the categorizations can evolve as technology advances and market trends change. This study presents the production, revenue, price, market share, and growth rate of each type of product, basically divided into

What Factors are the power source for the High Purity Magnesium Oxide Market's Growth?

• Oriented Silicon Steel
• Pharmaceutical Industry
• Food Industry
• Electrician Magnesium
• Hydrotalcite
• Rubber Industry
• Chlorinated Polyethylene Cable
• Others
• Oriented Silicon Steel is the greatest segment of High Purity Magnesium Oxide application, with a share of 41% in .

These applications highlight the versatility of High Purity Magnesium Oxide and their potential to enhance visual experiences across a wide range of settings and industries. This study focuses on the status and outlook for key applications and end users, consumption (sales), market share, and growth rate for each application, based on end users and applications

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High Purity Magnesium Oxide Market Competitive and Segmentation Analysis:

• How do you determine the list of the key players included in the report?

With the aim of clearly revealing the competitive situation of the industry, we concretely analyze not only the leading enterprises that have a voice on a global scale, but also the regional small and medium-sized companies that play key roles and have plenty of potential growth.

High Purity Magnesium Oxide Market Overview:

Market Analysis and Insights: Global High Purity Magnesium Oxide Market

The High Purity Magnesium Oxide market was valued at USD 363 million in and is projected to reach USD 507.4 million by , at a CAGR of 4.9% during the -. In this study, has been considered as the base year and to as the forecast period to estimate the market size for High Purity Magnesium Oxide.

In terms of production side, this report researches the High Purity Magnesium Oxide capacity, production, growth rate, market share by manufacturers and regions (or countries), from to , and forecast to .

In terms of sales side, this report focuses on the sales of High Purity Magnesium Oxide by regions (countries), company, by Type and by Application. from to and forecast to .

The global High Purity Magnesium Oxide market is thoroughly, accurately, and comprehensively assessed in the report with a large focus on market dynamics, market competition, regional growth, segmental analysis, and key growth strategies. Buyers of the report will have access to verified market figures, including global market size in terms of revenue and volume. As part of production analysis, the authors of the report have provided reliable estimations and calculations for global revenue and volume by Type segment of the global High Purity Magnesium Oxide market. These figures have been provided in terms of both revenue and volume for the period -. Additionally, the report provides accurate figures for production by region in terms of revenue as well as volume for the same period. The report also includes production capacity statistics for the same period.

Production by Region

 

Key Benefits of This Market Research Report:

• Competitive environment and prominent players' strategies.
• We cover potential and specialized markets as well as geographical areas with encouraging growth.
• Market size in terms of value across time, at the present time, and in the future comprehensive overview of the market for web analytics software.
• Overview of the Web Analytics Software Market's geographical forecast.

• What are your main data sources?

Both Primary and Secondary data sources are being used while compiling the report.

Primary sources include extensive interviews of key opinion leaders and industry experts (such as experienced front-line staff, directors, CEOs, and marketing executives), downstream distributors, as well as end-users. Secondary sources include the research of the annual and financial reports of the top companies, public files, new journals, etc. We also cooperate with some third-party databases.

Geographically, the detailed analysis of consumption, revenue, market share and growth rate, historical data and forecast (-) of the following regions are covered :

• North America (United States, Canada and Mexico)
• Europe (Germany, UK, France, Italy, Russia and Turkey etc.)
• Asia-Pacific (China, Japan, Korea, India, Australia, Indonesia, Thailand, Philippines, Malaysia and Vietnam)
• South America (Brazil, Argentina, Columbia etc.)
• Middle East and Africa (Saudi Arabia, UAE, Egypt, Nigeria and South Africa)

This High Purity Magnesium Oxide Market Research/Analysis Report Contains Answers to your following Questions

• What are the global trends in the High Purity Magnesium Oxide market? Would the market witness an increase or decline in the demand in the coming years?
• What is the estimated demand for different types of products in Leather Coatings? What are the upcoming industry applications and trends for High Purity Magnesium Oxide market?
• What Are Projections of Global High Purity Magnesium Oxide Industry Considering Capacity, Production and Production Value? What Will Be the Estimation of Cost and Profit? What Will Be Market Share, Supply and Consumption? What about Import and Export?
• Where will the strategic developments take the industry in the mid to long-term?
• What are the factors contributing to the final price of Leather Coatings? What are the raw materials used for High Purity Magnesium Oxide manufacturing?
• How big is the opportunity for the High Purity Magnesium Oxide market? How will the increasing adoption of High Purity Magnesium Oxide for mining impact the growth rate of the overall market?
• How much is the global High Purity Magnesium Oxide Market worth? What was the value of the market in ?
• Who are the major players operating in the High Purity Magnesium Oxide market? Which companies are the front runners?
• Which are the recent industry trends that can be implemented to generate additional revenue streams?
• What Should Be Entry Strategies, Countermeasures to Economic Impact, and Marketing Channels for High Purity Magnesium Oxide Industry?

Customization of the Report

• Can I modify the scope of the report and customize it to suit my requirements?

Yes. Customized requirements of multi-dimensional, deep-level and high-quality can help our customers precisely grasp market opportunities, effortlessly confront market challenges, properly formulate market strategies and act promptly, thus to win them sufficient time and space for market competition.

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Reasons to Buy This High Purity Magnesium Oxide Market Report:

Informed Decision-making: The High Purity Magnesium Oxide market research report provides valuable insights into industry trends, consumer behavior, and competitor analysis. This information can help companies make decisions about product development, pricing, and marketing strategies.

Competitive Advantage: By identifying market gaps and opportunities, market research reports can provide a competitive edge that can help companies differentiate themselves from competitors and gain market share.

Industry Expertise: High Purity Magnesium Oxide market research report is prepared by industry experts who have a thorough understanding of the market and its dynamics. These reports provide an unbiased view of the companys goals, which can be useful for companies that want to gain a deeper understanding of the market.

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Detailed TOC of Global High Purity Magnesium Oxide Market Insights and Forecast to

Table of Content

1 High Purity Magnesium Oxide Market Overview

1.1Product Overview and Scope of High Purity Magnesium Oxide

1.2 High Purity Magnesium Oxide Segment by Type

1.3 High Purity Magnesium Oxide Segment by Application

1.4 Global High Purity Magnesium Oxide Market Size Estimates and Forecasts

1.5 Assumptions and Limitations

2 High Purity Magnesium Oxide Market Competition by Manufacturers

2.1 Global High Purity Magnesium Oxide Sales Market Share by Manufacturers (-)

2.2 Global High Purity Magnesium Oxide Revenue Market Share by Manufacturers (-)

2.3 Global High Purity Magnesium Oxide Average Price by Manufacturers (-)

2.4 Global High Purity Magnesium Oxide Industry Ranking VS VS

2.5 Global Key Manufacturers of High Purity Magnesium Oxide, Manufacturing Sites Headquarters

2.6 Global Key Manufacturers of High Purity Magnesium Oxide, Product Type and Application

2.7 High Purity Magnesium Oxide Market Competitive Situation and Trends

2.8 Manufacturers Mergers, Acquisitions, Expansion Plans

3 High Purity Magnesium Oxide Retrospective Market Scenario by Region

3.1 Global High Purity Magnesium Oxide Market Size by Region: Versus Versus

3.2 Global High Purity Magnesium Oxide Global High Purity Magnesium Oxide Sales by Region: -

3.3 Global High Purity Magnesium Oxide Global High Purity Magnesium Oxide Revenue by Region: -

3.4 North America High Purity Magnesium Oxide Market Facts and Figures by Country

3.5 Europe High Purity Magnesium Oxide Market Facts and Figures by Country

3.6 Asia Pacific High Purity Magnesium Oxide Market Facts and Figures by Country

3.7 Latin America High Purity Magnesium Oxide Market Facts & Figures by Country

3.8 Middle East and Africa High Purity Magnesium Oxide Market Facts and Figures by Country

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4 Segment by Type

4.1 Global High Purity Magnesium Oxide Sales by Type (-)

4.2 Global High Purity Magnesium Oxide Revenue by Type (-)

4.3 Global High Purity Magnesium Oxide Price by Type (-)

5 Segment by Application

5.1 Global High Purity Magnesium Oxide Sales by Application (-)

5.2 Global High Purity Magnesium Oxide Revenue by Application (-)

5.3 Global High Purity Magnesium Oxide Price by Application (-)

6 Key Companies Profiled

Continued...

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Terpenoids and Steroids Volume 4

A Review of the Literature Published between September and August

By K. H. Overton

The Royal Society of Chemistry

Copyright © The Chemical Society
All rights reserved.
ISBN: 978-0--286-6

Contents

Part I Terpenoids,
Chapter 1 Monoterpenoids By A. F. Thomas, 3,
Chapter 2 Sesquiterpenoids By R. W. Mills and T. Money, 77,
Chapter 3 Diterpenoids By J. R. Hanson, 145,
Chapter 4 Sesterterpenoids By J. R. Hanson, 171,
Chapter 5 Triterpenoids By J. D. Connolly, 183,
Chapter 6 Carotenoids and Polyterpenoids By G. Britton, 221,
Chapter 7 Biosynthesis of Terpenoids and Steroids By D. V. Banthorpe and B. V. Charlwood, 250,
Part II Steroids,
Chapter 1 Steroid Properties and Reactions By D. N. Kirk, 311,
Chapter 2 Microbiological Reactions with Steroids By L. L. Smith, 394,
Chapter 3 Steroid Conformations from X-Ray Analysis Data By C. Romers, C. Altona, H. J. C. Jacobs, and R. A. G. de Graaff, 531,
Reviews on Terpenoid Chemistry, 301,
Errata, 584,
Author Index, 585,


CHAPTER 1

Part I

TARPENOIDS

1

Monoterpenoids

BY A. F. THOMAS

This year, the section on general chemistry has been enlarged, and some reactions that are not specific to monoterpenoids have been included. Physical methods are given a separate section. Unfortunately it must be noted that Chemical Abstracts contains an increasing number of errors, as well as frequently citing insufficient information for the abstract to be useful. So far as possible, attention has been drawn to these points in each individual case.

The abstracts of the Proceedings of the 4th Congress on Essential Oils (Tbilisi, ) have appeared, but much of this work is now out of date.

1 Physical Measurements: Spectra etc., Chirality

The 13C n.m.r. spectra of citronellol, citronellal, and related substances have been discussed, and a study of the shifts of the alkene signals induced by AgI in the 13C n.m.r. spectra of a number of substances including the pinenes has been made. A very full discussion of the effect of shift reagents on the 1H and 13C n.m.r. spectra of borneol and isoborneol has shown that the complexes formed with the reagents are effectively axially symmetric, the magnetic axis being practically collinear with the oxygen&#;metal bond; an estimate of the contact contribution has been made. Coupling constants in 7,7-dimethylnorborneols have been examined using the [Eu(dpmh)3] shift agent.

In a study of the u.v. spectra of the complexes between boron trifluoride and unsaturated ketones, monoterpenoids are particularly unlucky : piperitone (1) does not fit the attempted correlation, and carvone (2) polymerizes under the conditions of measurement!

The mass spectra of monoterpenoids have been discussed, and the loss of EtCONH2 in the mass spectrum of (3) (a retro-Ritter reaction) has given rise to speculations, without the support of labelling studies. The Raman 'circular dichroism' of a number of optically active monoterpenoids has been examined. Circular intensity differentials (CID) Δα, = IRα - ILα/ (IRα + ILα), where (IRα, ILα) are the scattering intensities with α -polarization in right and left circularly polarized incident light, have been measured in the low-frequency Raman spectra of (+)- and (-)- α-pinene, (-)-β -pinene, (-)-borneol, and carvone. The circular differential Raman spectrum of carvone has been reported elsewhere.

Monoterpenoids are the most common of the chiral agents used for inducing asymmetry. Measurement of the n.m.r. spectra of esters of camphanic acid, such as (4), has been used to find the enantiomeric purity and absolute configuration of α-deuteriated primary alcohols, and separations of various alcohols and amines using esters of chrysanthemic acid are reported. An interesting mutual resolution can be effected with ([+ or -])-camphorsulphonic acid and α-( [+ or -])-Me2NCH2CHMeCPh(OH)CH2Ph. (+)-Carvomenthol and chloroacetic acid give carvomethylacetic acid (5), which is useful for resolving alanine. Mislow et al. have used menthyl methylphenylthioarsenite (6) in an extension to arsenic of their earlier method (see Vol. 2, p. 28) of making optically active phosphine oxides.

Probably the most interesting work taking advantage of the chirality of monoterpenoids has involved the attempts to induce asymmetry in organic synthesis. As a simple example, the rate of esterification of D-amino-acids with (-)-menthol is greater than that of L-acids, and this has led to a proposal for menthyl ester formation. The anion (8), obtained when menthyl acetate (7) is metallated, reacts with ethyl pyruvate to yield the menthyl ester of (S)-citramalic acid (9) in 26 % optical yield. Kergomard et al. found no asymmetric induction in the reaction between styrene, t-butyl hypobromite, and menthol [leading to (10)]. Oxidation of ([+ or -])-borneol with (R)-(+)-menthyl p-tolyl sulphoxide and dicyclohexylcarbodi-imide in the presence of phosphoric acid in benzene gave (-)-camphor in 7% optical yield, and the cyclization of homogeranic (-)- menthyl ester with stannic chloride to cis-tetrahydroactinidiolide (11) occurred with only ca. 12% optical yield, although this rose to 20.8% when the 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose ester was used. Asymmetric reductions of diphenylmethyl alkyl ketones by complexes of lithium aluminium hydride and cis-pinane-2,3-diol and benzyl alcohol gave up to 20% optical yields, 21 but far more successful was the reaction of ethylene and cyclo-octa-1,3-diene [to [12)], catalysed by certain π-allyl complexes of nickel where one ligand is a monoterpenoid phosphine, in which 70 % optical purity was achieved.

King and Sim have described a useful method for demonstrating the presence of a reactive intermediate in reactions involving chiral diastereomeric transition states; it provided a new piece of evidence for the intermediacy of a sulphene in the reaction between camphor-10-sulphonyl chloride and menthylamine.

The Reporter is ill-placed to criticize a chapter on the synthesis of monoterpenoids in a recently published book on the total synthesis ofnatural products.23a However, a delay of three years between the latest reference quoted and publication of a book is deplorable.

2 General Chemistry

Sukh Dev has reviewed alumina- and silica gel-induced rearrangements, many of which involve monoterpenoids. The Prins reaction of monoterpenoid hydrocarbons has also been reviewed.

Microwave discharge of carbon dioxide can function as a singlet oxygen source; photo-oxygenation by this means has been accomplished using limonene and γ-terpinene as substrates. A two-phase solvent system is useful for epoxidizing sensitive olefins (e.g. 6-methylhept-5-en-2-one) with m-chloroperbenzoic acid, but limonene gave the same epoxide in the same yield as with the single-phase system.

Several novel methods for the reduction and oxidation of oxygenated terpenoids have appeared. Potassium metal in graphite can be used to reduce camphor (a 60:40 exo : endo mixture is obtained), and oxidations of primary alcohols are effected by chromic oxide in graphite (citronellol yields 90% of the aldehyde in 24 h), but the preparation of the reagent can be dangerous. Potassium metal in hexamethylphosphoramide, with or without a co-solvent, has also been used to reduce terpenoid ketones ; with camphor, more endo- product is formed than in the potassium&#;graphite reduction. Hindered saturated secondary alcohols are oxidized by 2,3-dichloro-5,6-dicyano-1,4-benzo-quinone; thus borneol and isoborneol are 96% and 95 % oxidized in 8 h and neoisomenthol (i.e. the all-cis-isomer) and neoisocarvomenthol are 48% and 40% oxidized in the same time, whereas the all-equatorial alcohols menthol and carvomenthol are hardly affected in this time. Reduction of camphor with various silanes (Ph2SiH2, PhSiH3, PhMeSiH2, and Et2SiH2) in the presence of tris(triphenylphosphine)chlororhodium gives 73&#;90% of isoborneol (exo), but triethylsilane gives only 30% of isoborneol and phenyldimethylsilane does not reduce. Analogous results were obtained for menthone, but pulegone (13) presented some irregularities, mixtures of menthone (14) and pulegol (15) being produced in different amounts depending on the reagent. The rate of Meerwein&#;Ponndorf reduction (propan-2-ol&#;aluminium isopropoxide) for a variety of terpenoid ketones is unexpectedly high. The half-life of camphor, for example, (the slowest of those measured) was 145.8 min at 82°C. Triphenyltin hydride reduces the conjugated double bond of unsaturated aldehydes; thus citral gives citronellal, but in the case of β-cyclocitral (16), the reaction works less specifically, leading to a 1:1 mixture of the saturated aldehyde (17) and the unsaturated alcohol (18).

4-Dimethylaminopyridine is a useful catalyst in acylations; an 80% yield of linalyl acetate can be obtained (without rearrangement &#; see Vol. 3, p. 15) with its aid, using triethylamine as solvent and (presumably, for it is omitted from the experimental details!) acetic anhydride at room temperature for 14 h. Only catalytic amounts are needed, as was demonstrated by the preparation of menthyl monophthalate. Reaction of aminomethylene ketones with 4-aminouracil (19; X = O), the thio-analogue (20; X = S), or 2,4-diamino-6-hydroxypyrimidine (the enolized imino-analogue), yields '5-deazapteridines'; those corresponding to menthone (20) and camphor (21) have been reported 37 (see Vol. 3, p. 42).

The preparation of monoterpenoid aldehydes from ketones (R2CHCHO in place of R2C=O) using the Grignard reagent EtOCH2MgCl is discussed.

The Kondakov reaction is the reaction of crotonic anhydride with an olefin in the presence of zinc chloride. A number of monoterpenoid hydrocarbons react at their trisubstituted double bonds; thus 2,6-dimethylocta-2,7-diene gives the ketone (22), car-3-ene gives (23), and menth-1-ene gives both cis- and trans- isomers. Double bonds react with chlorosulphonyl isocyanate to give compounds containing a four-membered heterocyclic ring; camphene yields (24), and the products from α- and β-pinene and car-3-ene have also been described.

The reaction of vinylmagnesium bromide with unsaturated esters gives the corresponding divinylcarbinol; ethyl mentha-1,8-diene-7-carboxylate and ethyl pin-2-en-10-carboxylate have been treated in this way. A convenient method for the separation of terpenoid alcohols from mixtures via the carbamates is described.

3 Biogenesis, Occurrence, and Biological Activity

A brief section on monoterpenoids is included in a review of biogenetic-like syntheses of terpenoids. For the biosynthesis of monoterpenoids see Section 4 of Chapter 7, p. 260.

Granger and Passet have carried out a chemotaxonomic study on Thymus vulgaris, L. This plant gives very diverse essential oils, and analysis of the monoterpenoids permits the assignment of a plant to its chemotype. Somewhat similar is the approach of Banthorpe et al. in an examination of oils of Juniperus and Thuja species. The juniper leaf oils consist of two types characterized by the presence of either predominantly pinene derivatives or thujane derivatives. Blue spruce (Picea pungens) can be identified by analysis of the cortical oleoresin monoterpenoids. The genesis of monoterpenoids in the wood of common Russian conifers has been followed by direct analysis.

Attention is drawn to the remarks on straightforward chemical analysis of plant and animal material made in Volume 3 (p. 8). Among analyses that are of interest for the monoterpenoid chemist are the following : Carphephorus odoratissimus ('deertongue', a tobacco additive), Cinnamomum reticulatum from Taiwan [containing a remarkable 96.8% of (-)-linalool], Crocus sativus, Passiflora edulis f. flavicarpa (passion fruit), Pelargonium tomentosum [86.9% (-)-isomenthone, for which various possible stereochemical biogenetic routes are discussed], various Pinus spp. needle oils, and Pogostemon plectrantoides. A very complete analysis of certain fractions of burley tobacco has given a plethora of substances, including many 1,1,3-trimethyl- and 1,1,2,3-tetramethyl-hexane derivatives and the novel isoprenoid (25).

Secretions from the endocrine glands of staphylinid beetles, Bledius mandibularis and B. spectabilis, contain small amounts of citral and neral.

The full papers describing the preparation of the hypoglycaemically active arylsulphonylureido- and arylsulphonylamido-acyl derivatives of borneol and isoborneol (see Vol. 2, p. 7) have appeared. Details of the preparation of the juvenile hormone compounds mentioned in Vol. 3, p. 10 have been published, and some more geranylanilines (with heterocyclic substituents in the aromatic part of the molecule) having juvenile hormone activity have been made. The section on chrysanthemic acid includes other compounds having juvenile hormone activity.

Isobornyl chloroformate (26 ; R = COCl) is prepared from isoborneol and phosgene, and can be used as a protecting group for amino-acids which is removed by trift uoroacetic acid. Combined with propylenediamines, the amines (26; R = CONHCH2CH2CH2NR1R2) can be made which have local anaesthetic properties.

4 Acyclic Monoterpenoids

Terpene Synthesis from Isoprene. &#; The oligomerization of isoprene catalysed by nickel naphthenate and isoprenemagnesium in the presence of various phosphites as electron donors, known to give cyclic dimers (see Vol. 3, p. 12), has been re-examined. Oligomerization with cobalt chloride, sodium borohydride, and tripenylphosphine gives (27) as the main product when the ratio Ph3P: CoC12<1, but when this ratio is > 1 the tail-to-tail linked isoprenoid (28) and the 2,6-di-methyloctatriene (29) are the main products. Telomerization of isoprene by hydrogen chloride in the presence of stannic chloride is reported. Anionic telomerization with secondary amines in the presence of alkali-metal catalysts yields dimers having as their main components the 'lavandulyl' (30) and the 'geranyl' (31) structures. A similar report elsewhere contains what appears to be the incorrect structure for geranyldiethylamine. The isoprene hydrochloride dimer [(32) or (33)] can be reduced with magnesium in tetrahydrofuran containing ethyl bromide; treatment of the mixture with dry oxygen then yields lavandulol (34) and its isomers in > 40% yield. The 'regular' geranyl skeleton is produced when isoprene is allowed to react with alcohols over a PdC12&#;PhCN catalyst together with triphenylphosphine and sodium alkoxide. The main ethers thus formed have the skeleton (35). The geranyl triene (36) is also the main component of the complex mixture obtained by treating isoprene and phenol with a sodium phenate-[PdBr2L2] (L = Ph2PCH2CH2PPh2) catalyst, the amount of phenol determining the composition of the mixture of products. With sodium hydride at 40°C under pressure isoprene yields myrcene (37) and the trimer (38). Hydrative dimerization of isoprene using a cation-exchange resin catalyst is described, 71 and a review (in Japanese) on the oligomerization catalysed by lithium naphthalene has appeared.

Dienes react with β-keto-esters in the presence of P-phenyl-1-phospha-3-methylcyclopent-3-ene and palladium chloride, and the addition product (39) from isoprene and methyl acetoacetate can be readily converted into methyl-heptenone (40).

2,6-Dimethyloctanes. &#; The iovalerate of dehydronerol (41) has been isolated from the roots of Anthemis montana, L.; this is the first report of a dehydronerol derivative in nature. The digestive gland of the sea hare, Aplysia californica, contains brominated and chlorinated monoterpenoids characterized by the presence of a terminal vinyl bromide group, e.g. (42) and (43). These compounds and other halogenated monoterpenoids have been found in the red algae, Plocamium coccineum, on which the sea hare is known to graze. 5 The structure of one compound (44) has been fully established by X-ray diffraction. The three trienes (45), (46), and (47) have been isolated from Ledum pa lustre ; one of them (46) has been previously identified in Pinus ponderosa. A number of bifunctional carbonyl compounds (48)&#;(53) have been isolated from lavandin oil. They all [excepting the aldehyde acetate (48)] can be obtained by the photo-oxygenation of linalyl acetate, and, apart from (48), they may well be artefacts.

An attempt to prepare photochemically mixtures of allo-ocimenes (54) with exclusive Z-configuration about the central double bond [(54a), (54b)] failed with a variety of sensitizers, although some enrichment was noted. Vig et al. have synthesized myrcene (37) from the known ester (55; R = CO22 Et) via the corresponding aldehyde (55; R = CHO), by a vinyl Grignard reaction, oxidation, and Wittig reaction. The pyrolytic conversion of α-pinene into allo-ocimene (54) is well known ;in order to trap the intermediate ocimene, it is necessary to cool the pyrolysate very rapidly.

One method used to introduce oxygen into terpenoid hydrocarbons is by direct, acid-catalysed addition of water. With myrcene, water addition in the presence of Amberlite IR-120 gives a complex reaction mixture, consisting mostly of cyclized components; the hydrated products are mainly 1,8-cineol (56), mentha-1(7),2-dien-8-ol (57), and 2,6-dimethylocta-5,7-dien-2-ol (58). Acid-catalysed addition of acetic acid to (+)-2,6-dimethylocta-2,7-diene [(+)-(59)] gives the tertiary acetate (60) initially, but refluxing for 6&#;8 h causes stereo-specific cyclization to (61), together with formation of the two tetrahydroeucarvols (62). The rhodium(m) chloride-catalysed addition of ethanol to myrcene (37) leads to oligomerization and isomerization, together with a mixture of the ethyl ethers [(63), (64), (65), and (66)] but none of the derivatives corresponding to those from the palladium-catalysed addition of methanol (see Vol. 2, p. 10).

(Continues...)

Excerpted from

Terpenoids and Steroids Volume 4

by

K. H. Overton

. Copyright © The Chemical Society. Excerpted by permission of The Royal Society of Chemistry.
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