The Journal of Organic Chemistry

The Sodium—Ammonia Reduction of Bispropargyl-and Propargylallylamines. Steric and Conformational Effects1

GF Hennion, RH Ode

Index: Hennion,G.F.; Ode,R.H. Journal of Organic Chemistry, 1966 , vol. 31, p. 1975 - 1977

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Citation Number: 13

Abstract

c H 3 ab gave the isomeric hexamethyl-3-methylenepyrrolidine (b) in 61% yield. 3 The corresponding N-demethylamines, conformationally less restrained with NH in place of N- CH3, also gave good yields of cyclized products except that the product purities were not so high owing to some competitive reduction without cyclization. Since this new4 cyclization reaction seemed to hold promise for the facile synthesis of substituted pyrrolines and ...