The Journal of Organic Chemistry

Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis (sym-collidine) iodine (I) Hexafluorophosphate as Electrophile

Y Brunel, G Rousseau

Index: Brunel, Yves; Rousseau, Gerard Journal of Organic Chemistry, 1996 , vol. 61, # 17 p. 5793 - 5800

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Citation Number: 47

Abstract

Oxepanes have been obtained in good yields (40-95%) by iodoetherification of unsaturated alcohols using bis (sym-collidine) iodine (I) hexafluorophosphate (1) as electrophile, either by 7-exo-mode or 7-endo-mode cyclizations. 4-Oxepenes could also be formed from 4, 6- heptadien-1-ols; the presence of a substituent on the carbon 6 appeared necessary, while for steric reasons the presence of a substituent on the carbon 7 was unfavorable. ...