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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry