On the isolation of neat allylic fluorides

Abstract

Neat cinnamyl fluoride, geranyl fluoride, 5-carbomethoxy-3-fluorocyclohexene and parent 3-fluorocyclohexene undergo spontaneous decomposition on contact with borosilicate glass or catalytic quantities of moderately strong acids that consists in polycondensation with elimination of HF initiated by electrophilic abstraction of F −. Acid sensitivity of these allylic fluorides correlates with stability of respective allylic cations, exceeds that of parent benzyl fluoride, yet can be mitigated by the use of Teflon and PFA containers that permit their isolation and handling in the neat state.