Halogen Epoxides, 7. Rearrangements during the Reaction of Substituted 2-Chloro- and 2,3-Dichlorooxiranes with Silver Tetrafluoroborate
Reactions of tert-butyl-substituted and of isopropyl-substituted chlorooxiranes with silver tetrafluoroborate have been examined.Dehalogenations in the 2-positions of 2-chloro-2-tert-butyl- (5) and of 2-chloro-2-isopropyl-substituted oxiranes (35) occurred without changes of the carbon skeletons.By contrast, dehalogenations in the 2-positions of 2-chloro-3-tert-butyl- (12) and of 2-chloro-3-isopropyloxiranes (35) afforded partly rearranged products by 1,2-methyl- and/or 1,2-hydride shifts to the corresponding α-ketocarbenium ions.
Keul, Helmut,Pfeffer, Bernd,Griesbaum, Karl
p. 2193 - 2204
(2007/10/02)
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