Tetrahedron

S RN 1 reactions of aryl halides with carbanions initiated by sodium amalgam in liquid ammonia

E Austin, CG Ferrayoli, RA Alonso, RA Rossi

Index: Austin, Eduardo; Ferrayoli, Carlos G.; Alonso, Ruben A.; Rossi, Roberto A. Tetrahedron, 1993 , vol. 49, # 21 p. 4495 - 4502

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Citation Number: 27

Abstract

The reaction of 1-chloronaphthalene with acetone (2a) and acetophenone (2b) enolate ions was initiated by sodium amalgam [Na (Hg)] in liquid ammonia giving good yields of the substitution products 3a and 3b respectively. 2-Chloroquinoline and 2-chloropyridine gave good yields of substitution product with 2b, and moderate to good yields with 2a. 4- Bromobenzophenone and 2a gave 78% of the substitution product 5. With aryl halides ...

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