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Paper | Special issue | Vol 50, No. 2, 1999, pp.739-756
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)70
■ Cyclization of Tautomeric 1,5-Dinitrile Systems with Hydrogen Halides: A Definitive Mechanistic Rationalization?

Jordi Teixidó,* José I. Borrell, Blanca Serra, Josep Lluis Matallana, Carles Colominas, Francisco Carrión, Rosalia Pascual, Josep Lluis Falcó, and Xavier Batllori

*Departament de Química Orgànica, CETS Institut Quimic de Sarrià, Universidad Ramon Llull, Via Augusta 390, E-08017 Barcelona, Spain

Abstract

A new mechanistic rationalization for the cyclization with hydrogen halides of tauomeric 1,5-dinitriles of general structure (10) (Z=N), (14)(Z = C-CN), (16) (Z=N), and (18) (Z = C-CN) is proposed (Scheme 5). In such rationalization, three factors play a major role on the direction of cyclization : Position of the equilibrium of the tautomeric 1,5-dinitrile system, relative basicity of the cyano group involved, and planarity of the reaction zone.