The Journal of Organic Chemistry

Photostimulated reactions of N, N-disubstituted amide enolate anions with haloarenes by the SRN1 mechanism in liquid ammonia

RA Rossi, RA Alonso

Index: Rossi, Roberto A.; Alonso, Ruben A. Journal of Organic Chemistry, 1980 , vol. 45, # 7 p. 1239 - 1241

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Citation Number: 32

Abstract

The photostimulated reactions of chloro-, bromo-, and iodobenzenes, 1-chloronaphthalene, and 9-bromophenanthrene with the enolate anion of N-methyl-N-phenylacetamide in liquid ammonia gave good yields of substituted products. In the dark, iodobenzene gave 34% of substitution product, but chlorobenzene did not react. The enolate anion of N, N- dimethylacetamide was only partially soluble in liquid ammonia, but good yields of ...