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Attempted Halogen Exchange in Methyl Substituted Mono- and Dibromocyclobutanes
Hittich, Reinhard,Mach, Helmut,Griesbaum, Karl
, p. 2738 - 2747 (2007/10/02)
Reactions of AgBF4 with 1-bromo-1-methyl- (1a) and with 1,3-dibromo-1,3-dimethylcyclobutanes (2a, 3a) afforded a partial of complete exchange of bromine for fluorine, depending on the reactant ratios.In 1,3-dibromo-1,2-dimethyl- (4a - 7a) and in 1,2-dibromo-1,2-dimethylcyclobutanes (8a), however, only one bromine substituent was exchanged for fluorine.From 8a products having cyclopropane structures (9, 10) and acyclic dihalo compounds (11a, b) were also formed.Reactions of SbCl5 with 1,3-dibromo-1,3-dimethylcyclobutane (2a, 3a) afforded a complete, reactions with 1,3-dibromo-1,2-dimethyl- (7a) and with 1.2-dibromo-1,2-dimethylcyclobutane (8a), however, only a partial exchange of bromine for chlorine.From 8a acyclic products were additionally formed.
