PHOTOOXYGENATION OF 1-ALKYL-2,3-DIARYLCYCLOPROPANES VIA PHOTOINDUCED ELECTRON-TRANSFER - STEREOSELECTIVE FORMATION OF 4-ALKYL-3,5-DIARYL-1,2-DIOXOLANES AND THEIR CONVERSION TO 1,3-DIOLS

被引：26

作者：

ICHINOSE, N ^{[1
]}

MIZUNO, K ^{[1
]}

TAMAI, T ^{[1
]}

OTSUJI, Y ^{[1
]}

机构：

[1] UNIV OSAKA PREFECTURE,COLL ENGN,DEPT APPL CHEM,SAKAI,OSAKA 591,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 13期

关键词：

D O I：

10.1021/jo00300a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 9,10-dicyanoanthracene-sensitized photooxygenation of l-alkyl-2,3-diarylcyclopropanes in CH3CN afforded c-4-alkyl-r-3,t-5-diaryl-l,2-dioxolanes in excellent yields with high stereoselectivity, which upon hydrogenolysis on Pd-charcoal gave quantitatively the corresponding l,2-threo-2,3-erytftro-2-alkyl-l,3-diaryl-l,3-diols. The mechanistic feature of this photoreaction is described. © 1990, American Chemical Society. All rights reserved.

引用

页码：4079 / 4083

页数：5

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