Radical ring closures of 4-isocyanato carbon-centered radicals

被引：31

作者：

Minin, PL ^{[1
]}

Walton, JC ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 07期

关键词：

D O I：

10.1021/jo034002o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-(2-isocyanatophenyl)ethyl radical was generated from the corresponding bromide with tributyltin and tris(trimethylsilyl)silyl radicals and shown to ring close in the 6-endo-mode to afford 3,4-dihydro-1H-quinolin-2-one as the major product. Cyclization in the 5-exo-mode to produce 2,3-dihydroindole-1-carbaldehyde, after hydrogen abstraction, was a minor reaction. Rate constants for the two processes were estimated and compared with reaction enthalpies computed by the DFT method.

引用

页码：2960 / 2963

页数：4

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