EXCEPTIONALLY STABLE OZONIDES - INFLUENCE OF METHYL SUBSTITUENTS ON THE COURSE OF CYCLOPENTENE OZONOLYSES AND ON THE REACTIVITIES OF OZONIDES

被引：17

作者：

MAYR, H ^{[1
]}

BARAN, J ^{[1
]}

WILL, E ^{[1
]}

YAMAKOSHI, H ^{[1
]}

TESHIMA, K ^{[1
]}

NOJIMA, M ^{[1
]}

机构：

[1] OSAKA UNIV,FAC ENGN,SUITA,OSAKA 565,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 17期

关键词：

D O I：

10.1021/jo00096a059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ozonolyses of 1,2,3,3,4,4,5,5-octamethyl- (1a), 1,2,3,3,4,4,5-heptamethyl- (1b), and 1,2,3,3,4,4-hexamethyl cyclopentenes (1c) in methanol did not yield the ordinary hemiperacetals but gave the corresponding ozonides 6a-c instead. The ozonides 6a,b were extremely stable nd remained intact even when refluxed with triphenylphosphine in tetrahydrofuran. Cycloreversion of the primary ozonides from unsymmetrically substituted 1,2,3,3-tetramethylcyclopentene (1d) and 1,5,5-trimethylcyclopentene (1g) was highly regioselective to yield the intermediate omega-oxo carbonyl oxides with the geminal methyl groups remote from the carbonyl oxide groups.

引用

页码：5055 / 5058

页数：4

共 31 条

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Bailey P. S., 1978, OZONATION ORGANIC CH, V1

[2]

Bailey P.S, 1982, OZONATION ORGANIC CH, V2

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