A new tin-free source of amidyl radicals

被引：80

作者：

Gagosz, F ^{[1
]}

Moutrille, C ^{[1
]}

Zard, SZ ^{[1
]}

机构：

[1] Ecole Polytech, CNRS, Synth Organ Lab, F-91128 Palaiseau, France

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026221m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The readily available N-(O-ethyl thiocarbonylsulfanyl)amides are powerful amidyl radical precursors that undergo 5-exo cyclization to give pyrrolidinone derivatives via a radical-chain reaction initiated by a small amount of lauroyl peroxide.

引用

页码：2707 / 2709

页数：3

共 19 条

[1] IMINYL, AMIDYL, AND CARBAMYL RADICALS FROM O-BENZOYL OXIMES AND O-BENZOYL HYDROXAMIC ACID-DERIVATIVES [J].

BOIVIN, J ;

CALLIERDUBLANCHET, AC ;

QUICLETSIRE, B ;

SCHIANO, AM ;

ZARD, SZ .

TETRAHEDRON, 1995, 51 (23) :6517-6528

[2] Spirolactams by a novel ipso-radical cyclisation and loss of aromaticity [J].

Boivin, J ;

Yousfi, M ;

Zard, SZ .

TETRAHEDRON LETTERS, 1997, 38 (34) :5985-5988

[3] Synthesis of heterocycles by radical cyclisation [J].

Bowman, WR ;

Bridge, CF ;

Brookes, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01) :1-14

[4] AMIDYL AND CARBAMYL RADICALS BY STANNANE MEDIATED CLEAVAGE OF O-BENZOYL HYDROXAMIC ACID-DERIVATIVES [J].

CALLIER, AC ;

QUICLETSIRE, B ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1994, 35 (33) :6109-6112

[5] A NEW SOURCE OF NITROGEN CENTERED RADICALS [J].

CALLIERDUBLANCHET, AC ;

QUICLETSIRE, B ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1995, 36 (48) :8791-8794

[6]

Clark AJ, 1999, SYNLETT, P444

[7]

Clark AJ, 1999, SYNLETT, P441

[8]

CONG XH, UNPUB

[9] CHEMISTRY OF AMIDYL RADICALS PRODUCED FROM N-HYDROXYPYRIDINE-2-THIONE IMIDATE ESTERS [J].

ESKER, JL ;

NEWCOMB, M .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4933-4940

[10] MULTIPLE REACTION CHANNELS OF (N-ACYL-N-ALKYLCARBAMOYL)OXYL RADICALS FROM N-ACYL PTOC CARBAMATES [J].

ESKER, JL ;

NEWCOMB, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2779-2786

← 1 2 →