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 phosphine cage moieties N3P(MeNCH2CH2)3N. The dominant reaction in the decomposition of this unusually thermally stable intermediate in the presence of HA is the formation of nitrogen and the salt [H2NP(MeNCH2CH2)3N]A in addition to benzene. Evidence for a transannulated cage intermediate is presented.