Polyfluorocycloalkenes. Part XII. Reaction of decafluorocyclohexene with alkanediols in the presence of base

Abstract

Decafluorocyclohexene and sodium hydride in 2-acetoxyethanol and in propane-1,3-diol gave multicomponent mixtures comprising several partially fluorinated dioxa-heterocycles resulting from the base-assisted intramolecular reactions of the first formed 1- and 3-alkoxynonafluorocyclohexenes. With butane-1,4-diol only 1- and 3-(4-hydroxybutoxy)nonafluorocyclohexenes were formed; no cyclisation reactions were observed. These reactions emphasise some of the limitations of nucleophilic displacement reactions in the synthesis of heterocycles.