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Paper | Special issue | Vol 47, No. 1, 1998, pp.181-186
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7629
5-endo-trig Radical Cyclization of 2-Chloro- and 2,2-Bis(phenylthio)-N-methyl- N-(6-phenylcyclohex-1-en-1-yl)-acetamides

Masazumi Ikeda,* Shinji Ohtani, Michiyo Okada, Emi Minakuchi, Tatsunori Sato, and Hiroyuki Ishibashi

*Kyoto Pharmaceutical University, Misasagi-Shichonocho, Yamashina, Kyorto 607-8414, Japan


Treatment of 2-chloro-N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide (4a) with Bu3SnH in the presence of AIBN gave a 2.5: 1 mixture of cis- and trans-fused N-methyl-7-phenyloctahydroindol-2-ones (5a and 5b) (13% combined yield), N-methyl-N-(2-phenylcyclohex-1-en-1-yl)acetamide (6) (19%), N-methyl-N-(6-phenylcyclohex-1-en-1-yl)acetamide (7) (13%), and N-(cyclohex-1-en-1-yl)-N-methyl-2-phenylacetamide (8) (4%). Similar treatment of the 2,2- bis(phenylthio)acetamide (4b) gave a 1:1 mixture of 5a and 5b (61% combined yield) along with 6 (24%) and 7 (trace). Possible mechanisms for the formation of the products (6)-(8) are also discussed.