Canadian Journal of Chemistry

Superacid-induced ring-opening reactions of fluorinated heterocycles

SP Kotun, DD DesMarteau

Index: Kotun, Stefan P.; DesMarteau, Darryl D. Canadian Journal of Chemistry, 1989 , vol. 67, p. 1724 - 1728

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Citation Number: 8

Abstract

HF/AsF5 and HF/SbF5 superacid mixtures react with fluorinated small-ring heterocycles such as 1, 2-oxazetidines and oxetanes with consequent addition of HF to give alcohol and amine ring-opened products in high yield. Excess HF serves as solvent and reactant. Ring compounds containing both nitrogen and oxygen as heteroatoms protonate predominantly on nitrogen; a case with competing O-protonation arises in the case of a chloro-substituted ...