Effect of variations of the size and structure of the principal alkyl group on alkene elimination from the immonium ions CH3CH2CHN+(CH3)R, CH3CH2CH2CHN+(CH3)R and CH3CH2CH2CH2CHN+(CH3)R11Dedicated to Professor Henri Edouard Audier on the occasion of his 60th birthday.

The reactions of three homologous series of metastable immonium ions of general structure, CH3(CH2)mCHN+(CH3)R, [m = 1–3; R = n-CnH2n+1, n = 1–10, 12, and 14, iso-C5H11, CH2CH(CH3)C2H5, neo-C5H11, and CH2CH2C(CH3)3] are reported and discussed. The first member of each homologous series is anomalous in undergoing several reactions, including elimination of molecular hydrogen and a methyl radical. In contrast, higher members of all three series …