PREPARATION OF OXEPANES, OXEPENES, AND OXOCANES BY IODOETHERIFICATIONUSING BIS(SYM-COLLIDINE)IODINE(I) HEXAFLUOROPHOSPHATE AS ELECTROPHILE

Authors
BRUNEL Y ROUSSEAU G
Citation
Y. Brunel et G. Rousseau, PREPARATION OF OXEPANES, OXEPENES, AND OXOCANES BY IODOETHERIFICATIONUSING BIS(SYM-COLLIDINE)IODINE(I) HEXAFLUOROPHOSPHATE AS ELECTROPHILE, Journal of organic chemistry, 61(17), 1996, pp. 5793-5800
Citations number
78
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
17
Year of publication
1996
Pages
5793 - 5800
Database
ISI
SICI code
0022-3263(1996)61:17<5793:POOOAO>2.0.ZU;2-7
Abstract
Oxepanes have been obtained in good yields (40-95%) by iodoetherificat ion of unsaturated alcohols using bis(sym-collidine)iodine(I) hexafluo rophosphate (1) as electrophile, either by 7-exo-mode or 7-endo-mode c yclizations. 4-Oxepenes could also be formed from 4,6-heptadien-1-ols; the presence of a substituent on the carbon 6 appeared necessary, whi le for steric reasons the presence of a substituent on the carbon 7 wa s unfavorable. Oxocanes could be obtained in moderate yields (18-27%).