α-Scission of sulfonyl radicals:: a versatile process for organic synthesis

被引：62

作者：

Bertrand, F

Le Guyader, F

Liguori, L

Ouvry, G

Quiclet-Sire, B

Seguin, S

Zard, SZ ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Ecole Polytech, CNRS, Lab Synthese Organ, F-91128 Palaiseau, France

来源：

COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE | 2001年 / 4卷 / 07期

关键词：

alkylsulfonyl radicals; trifluoromethanesulfonyl radicals; radical chains; allylation; vinylation; alkynylation; azidation;

D O I：

10.1016/S1387-1609(01)01270-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reversible addition of aliphatic radicals to sulphur dioxide can be exploited to design a variety of tin-free chain reactions. This brief review summarises some of the possibilities, namely radical allylation, vinylation, alkynylation, and azidation of various substrates. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevier SAS.

引用

页码：547 / 555

页数：9

共 56 条

[21]

KECK GE, 1982, J ORG CHEM, V47, P3590, DOI 10.1021/jo00139a053

[22] A FREE-RADICAL ADDITION FRAGMENTATION REACTION FOR THE PREPARATION OF VINYL SULFONES AND PHOSPHINE OXIDES [J].

KECK, GE ;

BYERS, JH ;

TAFESH, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1127-1128

[23] NOVEL RADICAL CYCLIZATIONS OF ALKYL AZIDES - A NEW ROUTE TO N-HETEROCYCLES [J].

KIM, S ;

JOE, GH ;

DO, JY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5521-5522

[24] Approximate rate constants for intermolecular additions of alkyl radicals to phenylsulfonyl oxime ethers [J].

Kim, S ;

Lee, IY .

TETRAHEDRON LETTERS, 1998, 39 (12) :1587-1590

[25] Novel radical reaction of phenylsulfonyl oxime ethers. A free radical acylation approach [J].

Kim, S ;

Lee, IY ;

Yoon, JY ;

Oh, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5138-5139

[26] Free radical-mediated ketone synthesis from alkyl iodides via sequential radical acylation approach [J].

Kim, S ;

Yoon, JY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (25) :5982-5983

[27]

KIM S, 1997, SYNLETT, V475

[28]

Kim Sinae, COMMUNICATION

[29] STEREOSELECTIVE PREPARATION OF THE ABCE TETRACYCLE OF ASPIDOSPERMIDINE AND RELATED ALKALOIDS [J].

KIZIL, M ;

MURPHY, JA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (14) :1409-1410

[30]

Knight D.W., 1991, COMPREHENSIVE ORGANI, V3, P481

← 1 2 3 4 5 6 →