FURANS FROM NOVEL [3+2]-PHOTOCYCLOADDITION OF ALKENES TO 2-(1-ALKYNYL)CYCLOHEXENONES

被引：27

作者：

MARGARETHA, P ^{[1
]}

REICHOW, S ^{[1
]}

AGOSTA, WC ^{[1
]}

机构：

[1] LABS ROCKEFELLER UNIV, NEW YORK, NY 10021 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期

关键词：

D O I：

10.1021/jo00097a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photocycloaddition of 2-alkynyl-substituted cyclohexenones 8c-11c with isobutylene (2) and tetramethylethylene (3a) leads to tricyclic furans 15a-18a and 15b-17b; respectively, in gas chromatographic yields of similar to 90%. A suggested mechanism for this novel-process is shown in eq 2. Tetramethoxyethylene (3b) gives only oxetanes 22 and 23, and the 3-methyl-substituted ketone 12c fails to react with 2 and 3a,b. tert-Butylethylene gives [2 + 2] adduct 24 with 10c.

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页码：5393 / 5396

页数：4

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