Reactions of allylic quaternary ammonium salts with alcohols in the synthesis of terpene ethers

被引：0

作者：

Petrushkina, E. A. ^{[1
]}

Khomishin, D. V. ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Bldg 1,28 Ul Vavilova, Moscow 119334, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2024年 / 73卷 / 10期

关键词：

terpenoids; ethers; irregular terpenes; alkylation of alcohols; PALLADIUM-CATALYZED TELOMERIZATION; SECONDARY-AMINES; ISOPRENE;

D O I：

10.1007/s11172-024-4410-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of quaternary ammonium salts bearing 2,7-dimethylocta-2,7-dien-1-yl moiety with primary alcohols (isoamyl and crotyl alcohols and geraniol) can be directed mainly to the allylic position to afford the corresponding ethers with the displacement of the ammonium leaving group. The reaction took place in the presence of NaOH under solvent-free conditions upon reflux or at heating at 150 degrees C. An important factor of regio-selectivity is a high steric hindrance of such ammonium group leaving group as R2(Allyl)N+. In the case of the derivative with Et2MeN+ group, alcohols attack the alkyl substituent.

引用

页码：2936 / 2940

页数：5

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