Preparation of functionalized trans-perhydroindans from substituted benzoic acids: reductive alkylation-halolactonization-free radical cyclization

CP Chuang, JC Gallucci, DJ Hart

Index: Chuang, Che-Ping; Gallucci, Judith C.; Hart, David J. Journal of Organic Chemistry, 1988 , vol. 53, # 14 p. 3210 - 3218

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Citation Number: 27

Abstract

Reductive alkylation of m-toluic acid (7), m-anisic acid (81, benzoic acid (9), and 2, 3- dimethylbenzoic acid (31) with selected alkyl halides followed by iodolactonization and side- chain modification gave free radical precursors 13, 14, 19, 27, and 34. Treatment of 13, 14, and 19 with tri-n-butyltin hydride and AIBN gave mixtures of perhydroindans and perhydronaphthalenes. Similar treatment of 27 and 34 gave trans-perhydroindans 28 and ...