Short path syntheses of alpha-diozonides by sequential ozonolyses of acetylenes and O-methyl oximes

被引：4

作者：

Dong, YX ^{[1
]}

Griesbaum, K ^{[1
]}

McCullough, KJ ^{[1
]}

机构：

[1] HERIOT WATT UNIV,DEPT CHEM,EDINBURGH EH14 4AS,MIDLOTHIAN,SCOTLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 11期

关键词：

D O I：

10.1039/a700989e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ozonolyses of but-2-yen 1 in the presence of added carbonyl compounds 3 afford alpha-oxo ozonides 4. Subsequent cycloadditions between ozonides 4 and cyclohexanone oxide 6, generated in situ by ozonolysis of O-methylcyclohexanone oxime, yield in turn alpha-diozonides 7 into which have been incorporated the carbon skeletons of all three substrates involved, Ozonolyses of acyloxy-substituted but-2-ynes 9 yield the corresponding bicyclic alpha-oxo ozonides Il which subsequently participate in analogous cycloadditions with 6 to produce the corresponding alpha-diozonides 12. X-Ray crystallographic analysis of the crystalline diozonide 12a shows that it has been formed exclusively by exo-addition of 6 to 11a.

引用

页码：1601 / 1604

页数：4

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