Studies on the additive fluoro-Pummerer reaction of phenylsulfanylated lactams with difluoroiodotoluene

被引：15

作者：

Greaney, MF ^{[1
]}

Motherwell, WB ^{[1
]}

Tocher, DA ^{[1
]}

机构：

[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(01)01813-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two fluorine atoms are effectively introduced to the 3- and 4-positions of sulfur-containing lactams through the action of the hypervalent iodoarene reagent difluoroiodotoluene (DFIT). The reaction proceeds through the intermediacy of the isolable alpha-beta -unsaturated congener followed by an additive-Pummerer process. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8523 / 8526

页数：4

共 22 条

[1] ARYLIODOSODIFLUORIDES [J].

CARPENTER, W .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (08) :2688-+

[2] ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS, ALPHA-HYDROXYKETONES, AND 2-PHENYLSULFENYL ALDEHYDES AND PRIMARY ALCOHOLS [J].

CRAIG, D ;

DANIELS, K ;

MACKENZIE, AR .

TETRAHEDRON, 1993, 49 (48) :11263-11304

[3] FLUORINATED PENICILLINS AND OTHER BETA-LACTAMS - CHEMISTRY AND BIOLOGICAL-ACTIVITY [J].

DANELON, GO ;

MASCARETTI, OA .

JOURNAL OF FLUORINE CHEMISTRY, 1992, 56 (02) :109-140

[4]

De Lucchi O., 1991, ORG REACTIONS, V40, P157, DOI DOI 10.1002/0471264180.0R040.03

[5] Observations on the α-fluorination of α-phenylsulfanyl esters using difluoroiodotoluene [J].

Greaney, MF ;

Motherwell, WB .

TETRAHEDRON LETTERS, 2000, 41 (22) :4463-4466

[6] Studies on the oxidation and fluorination of α-phenylsulfanylacetamides using difluoroiodotoluene [J].

Greaney, MF ;

Motherwell, WB .

TETRAHEDRON LETTERS, 2000, 41 (22) :4467-4470

[7]

GREANEY MF, 2000, THESIS U LONDON UK

[8] Selective fluorination of beta-ketoesters using iodotoluene difluoride and a HF-amine complex [J].

Hara, S ;

Sekiguchi, M ;

Ohmori, A ;

Fukuhara, T ;

Yoneda, N .

CHEMICAL COMMUNICATIONS, 1996, (16) :1899-1900

[9]

Hara S, 1998, SYNLETT, P495

[10]

KOEN MJ, 1995, CHEM COMMUN, P1241

← 1 2 3 →