Alkylation of nitriles with gaseous carbenium ions. The Ritter reaction in the dilute gas state

F Cacace, G Ciranni, P Giacomello

Index: Cacace, Fulvio; Ciranni, Giovanna; Giacomello, Pierluigi Journal of the American Chemical Society, 1982 , vol. 104, # 8 p. 2258 - 2261

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Citation Number: 12

Abstract

Abstract: Radiolytically formed carbenium ions, such as sec-C3H7+, sec-C4H9+, and t- C4H9+, react in the gas phase with model aliphatic and aromatic nitriles yielding the corresponding nitrilium ions. The latter undergo efficient condensation with water that eventually leads to the formation of the corresponding N-alkylamides. The mechanism is analogous to the Ritter reaction in solution. The reactivity and selectivity of the gas-phase ...