L. Yao, M. Shi, M. Shi
Oct 1, 2009
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0
Influential Citations
10
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Journal
European Journal of Organic Chemistry
Abstract
Bis(4-methoxyphenyl)methanol (2a) can be transformed by BF3·OEt2-catalyzed reactions of (arylmethylene)cyclopropanes 1 to the corresponding polysubstituted cyclopentenes 3 as the major products along with methylenecyclobutanes and dienes as minor products. The reaction conditions are mild, yields are moderate to good. In the reactions of aliphatic methylenecyclopropanes with bis(4-methoxyphenyl)methanol (2a), cyclopentenes 3o–q were produced in good yields under the standard conditions. Interesting results were obtained from the reactions of 1-[cyclopropylidene(4-methoxyphenyl)methyl]-4-methoxybenzene (1e) with bis(4-alkoxyphenyl)methanols 2: polysubstituted cyclopentene derivatives 5 were obtained in good yields under mild reaction conditions. Plausible reaction mechanisms based on the deuterium-labeling and control experiments are proposed.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)