80607-04-1Relevant academic research and scientific papers
Sextet Rearrangements as Solvent Polarity Probes
Langhals, Heinz,Hadizamani, Katja
, p. 407 - 409 (2007/10/02)
The rate constant of the Chapman variant of the Beckmann rearrangement is used as a solvent polarity probe and is mainly influenced by the polarizability of the solvent.Analogies to SN reaction are discussed.
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.
