Preparation of Functionalized trans-Perhydroindans from Substituted Benzoic Acids: Reductive Alkylation-Halolactonization-Free Radical Cyclization

Che Ping Chuang, Judith C. Gallucci, David J. Hart

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

Reductive alkylation of m-toluic acid (7), m-anisic acid (8), 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 35, respectively, as the major products. Iodo lactone 47 was also prepared from ethyl m-iodobenzoate (38) and converted to angularly oxygenated perhydroindans 48 and 49 by using a free radical cyclization.

Original languageEnglish
Pages (from-to)3210-3218
Number of pages9
JournalJournal of Organic Chemistry
Volume53
Issue number14
DOIs
Publication statusPublished - 1988 Jun 1

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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