B. Witte, P. Margaretha
Jun 5, 1999
Citations
0
Influential Citations
6
Citations
Journal
Organic Letters
Abstract
Irradiation of 2-alkynylcyclohex-2-enones 1a and 1b in the presence of 2-methylbut-1-en-3-yne in benzene affords 6-methylenehexahydronaphthalen-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.