USE OF TERT-BUTYL SULFOXIDES AS LATENT SULFENYL CATION EQUIVALENTS

被引：6

作者：

BRICHARD, MH

MUSICK, M

JANOUSEK, Z

VIEHE, HG

机构：

[1] Laboratoire de Chimie Organique, Place L. Pasteur B-1348, Louvain-la-Neuve

来源：

SYNTHETIC COMMUNICATIONS | 1990年 / 20卷 / 16期

关键词：

D O I：

10.1080/00397919008053185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: This paper reports a new and practical method of trifluoroacetoxysulfenylation of olefins, starting from t-butyl sulfoxides. The latter, in a mixture of trifluoroacetic anhydride and trifluoroacetic acid, do not undergo the Pummerer reaction. Instead, sulfenyltrifluoroacetates 2 are formed and they add in situ to olefins. © 1990, Taylor & Francis Group, LLC. All rights reserved.

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页码：2379 / 2386

页数：8

相关论文

共 9 条

[1] ADDITIONS TO ALKENES VIA METAL ION-PROMOTED OXIDATION OF DIALKYL AND DIARYL DISULFIDES [J].

BEWICK, A ;

MELLOR, JM ;

OWTON, WM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (05) :1039-1044

[2]

ELSAMII ZKM, 1988, J CHEM SOC P1, P2509

[3] NEW ROUTES TO HETEROCYCLES VIA SULFENYLATION OF UNSATURATED AMIDES [J].

ELSAMII, ZKMA ;

ALASHMAWY, MI ;

MELLOR, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2517-2522

[4] TRIFLUOROACETOXYSULFENYLATION OF UNSATURATED NITRILES AND TRANSFORMATION OF THE ADDUCTS INTO LACTONES [J].

ELSAMII, ZKMA ;

ALASHMAWY, MI ;

MELLOR, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2523-2531

[5]

FURUKAWA N, 1979, TETRAHEDRON LETT, P3973

[6]

Kuhle E., 1973, CHEM SULFENIC ACIDS

[7] REACTION OF THIOLSULFINATES WITH TRIHALOACETIC ANHYDRIDES .2. ADDITION OF SULFENYL TRIHALOACETATES TO OLEFINS [J].

MORISHITA, T ;

FURUKAWA, N ;

OAE, S .

TETRAHEDRON, 1981, 37 (15) :2539-2546

[8] HYDROXYSULFENYLATION OF OLEFINS - OLEFIN CLEAVAGE WITH FUNCTIONAL-GROUP DIFFERENTIATION [J].

TROST, BM ;

OCHIAI, M ;

MCDOUGAL, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) :7103-7106

[9] NUCLEOPHILIC-ATTACK ON OLEFINS INITIATED BY DIMETHYL(METHYLTHIO)SULFONIUM FLUOROBORATE (DMTSF) - CYANOSULFENYLATION AND OXYSULFENYLATION AND OXOSULFENYLATION [J].

TROST, BM ;

SHIBATA, T ;

MARTIN, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (11) :3228-3230