Easy synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones by silica gel-promoted fragmentation of 3-alkyl-2-oxaadamant-1-yl mesylates

被引：21
|
作者：
Camps, P [1 ]
ElAchab, R [1 ]
FontBardia, M [1 ]
Gorbig, D [1 ]
Morral, J [1 ]
MunozTorrero, D [1 ]
Solans, X [1 ]
Simon, M [1 ]
机构：
[1] UNIV BARCELONA, FAC GEOL, DEPT CRISTALLOG MINERAL & DIPOSITS MINERALS, E-08028 BARCELONA, SPAIN
来源：
TETRAHEDRON | 1996年 / 52卷 / 16期
关键词：
D O I：
10.1016/0040-4020(96)00217-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A synthesis of 7-alkylbicyclo[3.3.1]non-6-en-3-ones 4b-f and 4j,k by reaction of the corresponding 3-alkyl-2-oxaadamant-1-yl mesylates 3 with silica gel in methylene chloride at room temperature, is described. The method failed to give enones 4a,g and the related compounds 4l,m, what can be rationalized on mechanistic grounds. Copyright (C) 1996 Elsevier Science Ltd
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页码：5867 / 5880
页数：14
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