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Synlett 2000; 2000(10): 1497-1499
DOI: 10.1055/s-2000-7651
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The Use of an Iodine Atom as a Leaving Group for Bu3SnH-Mediated 5-Endo-Trig Radical Cyclization of α-Halo Amides is not Recommended

Hiroyuki Ishibashi* , Hana Matsukida, Atsushi Toyao, Osamu Tamura, Yoshifumi Takeda
  • *Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan; Fax + 81 (76) 234-4476; E-mail: isibasi@dbs.p.kanazawa-u.ac.jp
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Publication Date:
31 December 2000 (online)

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Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-1-enyl) α-chloro amides occurred with a high degree of efficiency, whereas the corresponding α-iodo congeners gave only limited quantities of the cyclization products. The cyclizing ability of α-iodo amides can be restored with Bu3SnCl as an additive.

radical cyclization - 5-endo-trig - tributyltin chloride - rotamer