The Journal of Organic Chemistry

Reductive metalation of 1, 3-diphenylisobenzofuran. Stereoselective formation of cis products

JG Smith, RB McCall

文献索引：Smith, James G.; McCall, Robert B. Journal of Organic Chemistry, 1980 , vol. 45, # 20 p. 3982 - 3986

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被引用次数: 16

摘要

1, 3-Diphl? nylisobenzofuran was reduced in tetrahydrofuran by alkali metals to a dianion. This dianion on protonation, methylation, or carboxylation gave products which were predominantly cis. It is suggested that the dianion or the intermediate monoreacted monoanion adopts a preferred conformation in which steric interaction between the phenyl substituents is minimized and orbital overlap between the carbanion and the benzene ring ...