PHOTOCHEMICAL-SYNTHESIS OF OXIME ACETATES DERIVATIVES OF 1-CARBALDEHYDOBICYCLO[N.1.0]ALKANES BY THE AZA-DI-PI-METHANE REARRANGEMENT

被引：10

作者：

ARMESTO, D

RAMOS, A

机构：

[1] Departamento de Quimica Organica I, Facultad de Ciencias Quimicas, Universidad Complutense

来源：

TETRAHEDRON | 1993年 / 49卷 / 32期

关键词：

D O I：

10.1016/S0040-4020(01)87986-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first photochemical synthesis of some 1-carbaldehydobicyclo[n.1.0]alkane oxime acetates has been achieved by the aza-di-pi-methane (ADPM) rearrangement of oxime acetates of 2-(cyclopent-1-enyl)- and 2-(cyclohex-1-enyl)-2-methylpropanals. Further increase in ring-size affects adversely the reaction and the oxime acetate of 2-(cyclohept-1-enyl)-2-methylpropanal is unreactive by the ADPM path. The low efficiency of rearrangement of 2-(cyclohex-1-enyl)-2-methylpropanal can be overcome by incorporation of a benzo substituent and this compound, 2-(2-[3,4-dihydronaphthalenyl])-2-methylpropanal, undergoes the ADPM rearrangement efficiently.

引用

收藏

页码：7159 / 7168

页数：10

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