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Wanderungstendenzen cyclischer, polycyclischer und methylverzweigter Alkylreste bei der Beckmann-Umlagerung
Langhals, Heinz,Ruechardt, Christoph
, p. 3831 - 3854 (2007/10/02)
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.
