7, 7-Dimethyltricyclo[3.3.0.0.2, 8]octan-3-ones as Synthetic Intermediates. I. : Preparation and Cyclopropane Ring Opening of 7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.02, 8]octan-3-one

TAKESHI IMANISHI; MASAYUKI YAMASHITA; MUNETAKA MATSUI; FUSAKO NINBARI; TETSUAKI TANAKA; CHUZO IWATA

doi:10.1248/cpb.36.1351

7, 7-Dimethyltricyclo[3.3.0.0.^{2, 8}]octan-3-ones as Synthetic Intermediates. I. : Preparation and Cyclopropane Ring Opening of 7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.0^{2, 8}]octan-3-one

今西武, 山下正行, 松井宗隆, 仁張総子, 田中徹明, 岩田宙造

著者情報

キーワード: S_N2 reaction

ジャーナルフリー

1988 年 36 巻 4 号 p. 1351-1357

DOI https://doi.org/10.1248/cpb.36.1351

詳細

抄録

7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.0^{2, 8}]octan-3-one (4) was prepared from 4, 4-di-methyl-2-cyclopentenone in several steps. The Birch reduction of 4 resulted in exclusive formation of a bicyclo[3.3.0]octanone (14)through C₂-C₈ bond clevage, while its substitutional reactions yielded bicyclo[3.2.1]octanones (15) through C₁-C₂ bond cleavage as major products.

責任著者(Corresponding author)

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