Photochemical formation of 3,4,4a,5,6,8a-hexahydro-2H-naphthalen-1-ones from cyclohex-2-enones and 2-methylbut-1-en-3-yne

被引：13
|
作者：
Witte, B [1 ]
Margaretha, P [1 ]
机构：
[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany
来源：
ORGANIC LETTERS | 1999年 / 1卷 / 02期
关键词：
D O I：
10.1021/ol990003k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Irradiation of 2-alkynylcyclohex-2-enones 1a and 1b in the presence of 2-methylbut-1-en-3-yne in benzene affords 6-methylenehexahydronaph-thalen-1-ones 2 as main products while photolysis in methanol gives predominantly 1:1 diastereomeric mixtures of 6-methoxy-6-methylnaphthalenones 4 and 5, respectively, The key step in this stepwise [4 + 2]-cycloaddition is the 1,6-cyclization of biradical 6 to 1,2-cyclohexadiene 7.
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页码：173 / 174
页数：2
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