Preparation of trichlorothioacetmides and their unexpected rearrangement to thiooxamides

被引：6

作者：

Braverman, S ^{[1
]}

Cherkinsy, M ^{[1
]}

Kedrova, L ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 50期

基金：

以色列科学基金会;

关键词：

amides; thioamides; Favorskii rearrangement;

D O I：

10.1016/S0040-4039(98)02080-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of several N-monosubstituted trichlorothioacetamides by thionation of the corresponding acetamides, with the use of Heimgartner's reagent is described. In contrast to the corresponding amides which umdergo base-induced beta-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

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收藏

页码：9259 / 9262

页数：4

相关论文

共 18 条

[1]

BACKES J, 1991, HOUBENWEYL METHODE E, V16, P1

[2] A new synthesis of N-sulfinylamines via beta-elimination of chloroform from trichloromethanesulfinamides [J].

Braverman, S ;

Cherkinsky, M .

TETRAHEDRON LETTERS, 1997, 38 (03) :487-490

[3] A NOVEL SYNTHESIS OF MONOSUBSTITUTED SULFINES VIA AN UNUSUAL BETA-ELIMINATION OF CHLOROFORM FROM ALLYLIC AND BENZYLIC TRICHLOROMETHYL SULFOXIDES [J].

BRAVERMAN, S ;

GRINSTEIN, D ;

GOTTLIEB, HE .

TETRAHEDRON LETTERS, 1994, 35 (06) :953-956

[4]

Drobinca L., 1977, CHEM CYANATES THEIR, P1003

[5]

FRITZ H, 1978, B SOC CHIM BELG, V87, P525

[6] STERIC LIMITS IN THE REACTIONS OF AMINES WITH INSITU GENERATED ALPHA-LACTAMS - THE SYNTHESIS OF EXTREMELY STERICALLY HINDERED TERTIARY-AMINES [J].

GUZIEC, FS ;

TORRES, FF .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1604-1606

[7] Tetraphosphorus decasulfide, revival of an old thionating agent [J].

Hartke, K ;

Gerber, HD .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1996, 338 (08) :763-765

[8] Studies on Rubia akane (RA) derivatives .10. Backbone transformation of RA-VII, an antitumour cyclic hexapeptide, through thionation. X-ray crystal structure of [Tyr-3-Psi(CH2NH)-Ala-4]RA-VII [J].

Hitotsuyanagi, Y ;

Matsumoto, Y ;

Sasaki, S ;

Suzuki, J ;

Takeya, K ;

Yamaguchi, K ;

Itokawa, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1749-1755

[9] ELECTROCHEMICAL AND STEREOCHEMICAL INVESTIGATION ON THE MECHANISM OF THE DECAY OF 2-HALO AMIDE ANIONS - THE INTERMEDIACY OF AZIRIDINONES [J].

MARAN, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :6557-6563

[10]

PEDERSEN BS, 1978, B SOC CHIM BELG, V87, P293