SRN1 REACTIONS OF SOME PHOSPHORUS NUCLEOPHILES WITH IODOBENZENE AND BROMOBENZENE

被引：19

作者：

SWARTZ, JE ^{[1
]}

BUNNETT, JF ^{[1
]}

机构：

[1] UNIV CALIF SANTA CRUZ,SANTA CRUZ,CA 95064

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 25期

关键词：

D O I：

10.1021/jo00393a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four phosphanion nucleophiles, PhP(0Bu)O-, Ph2PO-, (EtO)2PS-, and (Me2N)2PO-, react with iodo- or bromobenzene in ammonia under brief irradiation to form substitution products Ph2PO(OBu), Ph3PO, PhPS(OEt)2, and PhPO(NMe2)2, respectively. Reactions of the first three nucleophiles with iodobenzene occur in nearly quantitative yield. Iodobenzene/bromobenzene reactivity ratios, measured in competition experiments, are 1 x 103 for PhP(OBu)O-, 5 X 102 for (Me2N)2PO-, and 45 for (EtO)2PS-. These reactions are believed to occur by the radical chain SRN1 mechanism. © 1979, American Chemical Society. All rights reserved.

引用

页码：4673 / 4677

页数：5

共 32 条

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[7] PHOTOSTIMULATED CONDENSATION OF ARYL IODIDES WITH POTASSIUM DIALKYL PHOSPHITES TO FORM DIALKYL ARYLPHOSPHONATES
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