Wanderungstendenzen cyclischer, polycyclischer und methylverzweigter Alkylreste bei der Beckmann-Umlagerung
The migration aptitudes of polycyclic bridgehead groups, cycloalkyl groups as well as of β-, γ- and δ-branched alkyl groups in the Chapman variant of the Beckmann rearrangement were determined.From these data it is concluded that at transition state 2 the migrating group is not resembling a planarised carbenium ion R+, but rather a pentacoordinated carbonium ion structure.Because only small geometrical changes occur in the migrating group vertical stabilisation of charge at transition state is believed to have significant influence on the migration aptitudes.
Langhals, Heinz,Ruechardt, Christoph
p. 3831 - 3854
(2007/10/02)
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