The Journal of Organic Chemistry

Aromatic radical nucleophilic substitution reactions initiated by sodium amalgam in liquid ammonia

E Austin, RA Alonso, RA Rossi

Index: Austin, Eduardo; Alonso, Ruben A.; Rossi, Roberto A. Journal of Organic Chemistry, 1991 , vol. 56, # 14 p. 4486 - 4489

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Citation Number: 25

Abstract

Neither 1-chloronaphthalene nor 2-chloroquinoline reacted with PhzP ions in liquid ammonia. However, in the presence of sodium amalgam [Na (Hg)], reaction did occur, and the substitution products l-naphthyldiphenylphosphine and 2quinolyldiphenylphosphine (isolated as the P-oxides), respectively, were obtained in good yield. p-Bromoanisole reacted with Na (Hg) amalgam in the presence of PhzP ions in liquid ammonia to give ...