INTRA-MOLECULAR DE-MAYO REACTIONS OF 3-ACETOXY-2-ALKENYL-2-CYCLOHEXENONES

被引：26

作者：

OPPOLZER, W

BIRD, TGC

机构：

[1] Département de Chimie Organique, Université de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 04期

关键词：

D O I：

10.1002/hlca.19790620429

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The photoaddition, hydrolysis, retro‐aldol sequences 1 → 2 → 3 and 4 → 5 + 6 → 7 proceeded in high yield and in a regiospecific manner. However, the enol acetate 8 on irradiation furnished the tricyclic ketoacetate 9 as the major product, presumably by a hydrogen shift in the intermediate diradical 11. Hydrolysis of the minor photoadduct 10 gave the dione 13. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1199 / 1202

页数：4

共 13 条

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[7] MELLOR M, 1978, CHEM COMMUN, P138
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OPPOLZER, W
GODEL, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (08) : 2583 - 2584
[9] OPPOLZER W, UNPUBLISHED
[10] ALKYLATION OF 1,5-DIMETHOXY-1,4-CYCLOHEXADIENE - CONVENIENT SYNTHESIS OF 2-ALKYL-1,3-CYCLOHEXANEDIONE AND 2-ALKENYL-1,3-CYCLOHEXANEDIONE
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GRIERSON, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) : 3755 - 3757

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