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Communication | Regular issue | Vol 14, No. 8, 1980, pp.1115-1121
Published online, 1st January, 1970
DOI: 10.3987/R-1980-08-1115
Ene Reaction of 1-Pyrazoline Derivatives with Tetracyanoethylene

Alma Calatroni and Remo Gandolfi*

*Dipartamento di Chimica Organica, Università di Pavia, V. le Taramelli 10, 27100 Pavia, Italy

Abstract

1-Pyrazoline derivatives 4 and 5 reacted with tetracyanoethylene to give, through a formal ene reaction followed by a loss of hydrogen cyanide, 1-tricyanovinyl-2-pyrazoline derivatives 6 and 7 as dominant products. By contrast, tetracyanoethylene played only a catalytic role in the reaction with 1-pyrazolines 11 promoting their tautomerization to 2-pyrazolines 13. The possible mechanisms of such reactions are discussed.