Facile formation of benzene from a novel cyclohexane derivative

Upon acidification, benzene forms at room temperature from the novel 1,3,5- cis-trisubstituted cyclohexane wherein the substituents are the azido phosp hine cage moieties N3P(MeNCH2CH2)(3)N. The dominant reaction in the decompo sition of this unusually thermally stable intermediate in the presence of H A is the formation of nitrogen and the salt [H2N=P(MeNCH2CH2)(3)N]A in addi tion to benzene. Evidence for a transannulated cage intermediate is present ed. (C) 2001 Published by Elsevier Science Ltd.