Reactions of 3,3,4,4-tetrafluorohexa-1,5-diene. Part II. Cyclisation to a four-membered ring in the thermal addition of pentafluoroiodoethane
Abstract
Pentafluoroiodoethane reacts at 210–220° with 3,3,4,4-tetrafluorohexa-1,5-diene to give unusual cyclisation products having a four-membered ring, contrary to analogous reactions of perfluoroalkyl iodides with hexa-1,5-diene and in spite of the unfavourable entropy change to give highly strained ring structure. Also minor amounts of an isomeric saturated monoadduct containing a five-membered ring and of acyclic monoadduct were isolated. The structures of the cyclic products were elucidated by spectroscopic and chemical methods.