Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

Samuel Braverman; Marina Cherkinsky; Ludmila Kedrova

doi:10.1016/s0040-4039(98)02080-2

Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

Samuel Braverman
, Marina Cherkinsky
, Ludmila Kedrova

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

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 undergo base-induced β-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed.

Original language	English
Pages (from-to)	9259-9262
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	50
DOIs	https://doi.org/10.1016/s0040-4039(98)02080-2
State	Published - 10 Dec 1998

Bibliographical note

Funding Information:
Acknowledgment : The financial support by the ISRAEL SCIENCE FOUNDATION of this work is gratefully acknowledged.

Funding

Acknowledgment : The financial support by the ISRAEL SCIENCE FOUNDATION of this work is gratefully acknowledged.

Funders
Israel Science Foundation

Keywords

Amides
Favorskii rearrangement
Thioamides

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10.1016/s0040-4039(98)02080-2

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title = "Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides",

abstract = "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 undergo base-induced β-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed.",

keywords = "Amides, Favorskii rearrangement, Thioamides",

author = "Samuel Braverman and Marina Cherkinsky and Ludmila Kedrova",

note = "Funding Information: Acknowledgment : The financial support by the ISRAEL SCIENCE FOUNDATION of this work is gratefully acknowledged.",

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T1 - Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

AU - Braverman, Samuel

AU - Cherkinsky, Marina

AU - Kedrova, Ludmila

N1 - Funding Information: Acknowledgment : The financial support by the ISRAEL SCIENCE FOUNDATION of this work is gratefully acknowledged.

PY - 1998/12/10

Y1 - 1998/12/10

N2 - 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 undergo base-induced β-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed.

AB - 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 undergo base-induced β-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed.

KW - Amides

KW - Favorskii rearrangement

KW - Thioamides

UR - https://www.scopus.com/pages/publications/0032506671

U2 - 10.1016/s0040-4039(98)02080-2

DO - 10.1016/s0040-4039(98)02080-2

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AN - SCOPUS:0032506671

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

Abstract

Bibliographical note

Funding

Keywords

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