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Communication | Special issue | Vol 54, No. 2, 2001, pp.629-633
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)103
Intramolecular Oxymercuration of 4-Hexen-1-ols: Kinetic vs. Thermodynamic Products Regulated by Mercuric Salts

Mugio Nishizawa,* Terumi Kashima, Masahiro Sakakibara, Akihito Wakabayashi, Kazuya Takahashi, Hiroko Takao, Hiroshi Imagawa, and Takumichi Sugihara*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan

Abstract

The rate and mode of intramolecular oxymercuration of 4-hexen-1-ol derivatives was greatly affected by mercuric salts. Mercuric acetate induced a slow reaction to give substituted tetrahydrofurans via 5-exo-trans cyclization. In contrast, 6-endo-trans cyclization proceeded exclusively by mercuric triflate with or without N,N,N’,N’-tetramethylurea.