Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(sym-collidine)iodine(I) Hexafluorophosphate as Electrophile
摘要:
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. Oxocanes could be obtained in moderate yields (18-27%).
Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(sym-collidine)iodine(I) Hexafluorophosphate as Electrophile
摘要:
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. Oxocanes could be obtained in moderate yields (18-27%).
作者:Daniel A. Singleton、Stephen C. Waller、Zongren Zhang、Doug E. Frantz、Shun-Wang Leung
DOI:10.1021/ja961616k
日期:1996.1.1
Preparation of Oxepanes, Oxepenes, and Oxocanes by Iodoetherification using Bis(<i>sym</i>-collidine)iodine(I) Hexafluorophosphate as Electrophile
作者:Yves Brunel、Gérard Rousseau
DOI:10.1021/jo960506t
日期:1996.1.1
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. Oxocanes could be obtained in moderate yields (18-27%).