FREE-RADICAL RING-EXPANSION LEADING TO NOVEL 6-MEMBERED AND 7-MEMBERED HETEROCYCLES

被引：40

作者：

DOWD, P

CHOI, SC

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON | 1991年 / 47卷 / 27期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4020(01)80951-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Free radical promoted ring-expansion of nitrogen-, oxygen- and sulfur-containing heterocyclic beta-keto esters is described. Treatment of the derived phenylselenomethyl derivatives with tri-n-butyltin hydride leads to smooth one-carbon ring expansion.

引用

收藏

页码：4847 / 4860

页数：14

相关论文

共 21 条

[1] CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBERTSON, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (21) :1404-1406

[2] CARBOCYCLIC RING EXPANSION REACTIONS VIA RADICAL CHAIN PROCESSES [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBERTSON, J .

TETRAHEDRON, 1989, 45 (04) :909-922

[3] REARRANGEMENT OF SUITABLY CONSTITUTED ARYL, ALKYL, OR VINYL RADICALS BY ACYL OR CYANO GROUP MIGRATION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

WESTWOOD, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2565-2575

[4] CYANO OR ACYL GROUP MIGRATION BY CONSECUTIVE HOMOLYTIC ADDITION AND BETA-FISSION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

GERBA, S ;

WESTWOOD, SW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (09) :666-667

[5] RELATIVE REACTIVITIES OF VARIOUS SULFIDES, SELENIDES AND HALIDES TOWARDS SH2 ATTACK BY TRIBUTYLTIN RADICALS [J].

BECKWITH, ALJ ;

PIGOU, PE .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (01) :77-87

[6] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[7] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (07) :489-513

[8] A NEW TRI-NORMAL-BUTYLTIN HYDRIDE BASED REARRANGEMENT OF BROMOMETHYL BETA-KETO-ESTERS - A SYNTHETICALLY USEFUL RING EXPANSION TO GAMMA-KETO ESTERS [J].

DOWD, P ;

CHOI, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3493-3494

[9] FREE-RADICAL RING EXPANSION BY 3 AND 4 CARBONS [J].

DOWD, P ;

CHOI, SC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6548-6549

[10] FREE-RADICAL RING-EXPANSION LEADING TO NOVEL 6-MEMBERED AND 7-MEMBERED HETEROCYCLES [J].

DOWD, P ;

CHOI, SC .

TETRAHEDRON LETTERS, 1989, 30 (45) :6129-6132