AROMATIC RADICAL NUCLEOPHILIC-SUBSTITUTION REACTIONS INITIATED BY SODIUM AMALGAM IN LIQUID-AMMONIA

被引：24

作者：

AUSTIN, E ^{[1
]}

ALONSO, RA ^{[1
]}

ROSSI, RA ^{[1
]}

机构：

[1] UNIV NACL CORDOBA,FAC CIENCIAS QUIM,DEPT QUIM ORGAN,SUC 16,CC 61,CORDOBA,ARGENTINA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Neither 1-chloronaphthalene nor 2-chloroquinoline reacted with Ph2P- ions in liquid ammonia. However, in the presence of sodium amalgam [Na(Hg)], reaction did occur, and the substitution products 1-naphthyldiphenylphosphine and 2-quinolyldiphenylphosphine (isolated as the P-oxides), respectively, were obtained in good yield. p-Bromoanisole reacted with Na(Hg) amalgam in the presence of Ph2P- ions in liquid ammonia to give anisole as the only product, but when benzonitrile was used as a redox catalyst, a good yield of the substitution product p-anisyldiphenylphosphine (isolated as the P-oxide) was obtained. It is believed that Na(Hg) amalgam initiated these S(RN)1 reactions. Preparative-scale reactions gave good yields of the substitution products.

引用

页码：4486 / 4489

页数：4

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