New contributions to the chemistry of 2-chloro-2-(chlorothio)propanedioic diesters and diamides

Mohamed A.M. Hawata; Abdel M. El-Torgoman; Salah M. El-Kousy; Abd El-Hamid Ismail; Jørgen Øgaard Madsen; Inger Søtofte; Alexander Erich Eugen Senning

New contributions to the chemistry of 2-chloro-2-(chlorothio)propanedioic diesters and diamides

Mohamed A.M. Hawata
, Abdel M. El-Torgoman
, Salah M. El-Kousy
, Abd El-Hamid Ismail
, Jørgen Øgaard Madsen
, Inger Søtofte
, Alexander Erich Eugen Senning

Department of Chemistry

Menoufia University

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The pyridine-catalyzed reaction between a number of propanedioic acid derivatives 1 and thionyl chloride has been investigated in detail. Contrary to popular belief the straightforward formation of the corresponding alpha-chloro sulfenyl chlorides 2 is the exception rather than the rule. The propanediamide 2e, not available by the "standard" reaction of le with thionyl chloride, is surprisingly formed by reaction of le with sulfur dichloride. The usefulness of 2 as thiosulfine 4 precursors has been demonstrated.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	13
Pages (from-to)	2039-2045
ISSN	1434-193X
Publication status	Published - 2002

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title = "New contributions to the chemistry of 2-chloro-2-(chlorothio)propanedioic diesters and diamides",

abstract = "The pyridine-catalyzed reaction between a number of propanedioic acid derivatives 1 and thionyl chloride has been investigated in detail. Contrary to popular belief the straightforward formation of the corresponding alpha-chloro sulfenyl chlorides 2 is the exception rather than the rule. The propanediamide 2e, not available by the {"}standard{"} reaction of le with thionyl chloride, is surprisingly formed by reaction of le with sulfur dichloride. The usefulness of 2 as thiosulfine 4 precursors has been demonstrated.",

author = "Hawata, \{Mohamed A.M.\} and El-Torgoman, \{Abdel M.\} and El-Kousy, \{Salah M.\} and Ismail, \{Abd El-Hamid\} and Madsen, \{J{\o}rgen {\O}gaard\} and Inger S{\o}tofte and Senning, \{Alexander Erich Eugen\}",

year = "2002",

language = "English",

volume = "13",

pages = "2039--2045",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH",

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TY - JOUR

T1 - New contributions to the chemistry of 2-chloro-2-(chlorothio)propanedioic diesters and diamides

AU - Hawata, Mohamed A.M.

AU - El-Torgoman, Abdel M.

AU - El-Kousy, Salah M.

AU - Ismail, Abd El-Hamid

AU - Madsen, Jørgen Øgaard

AU - Søtofte, Inger

AU - Senning, Alexander Erich Eugen

PY - 2002

Y1 - 2002

N2 - The pyridine-catalyzed reaction between a number of propanedioic acid derivatives 1 and thionyl chloride has been investigated in detail. Contrary to popular belief the straightforward formation of the corresponding alpha-chloro sulfenyl chlorides 2 is the exception rather than the rule. The propanediamide 2e, not available by the "standard" reaction of le with thionyl chloride, is surprisingly formed by reaction of le with sulfur dichloride. The usefulness of 2 as thiosulfine 4 precursors has been demonstrated.

AB - The pyridine-catalyzed reaction between a number of propanedioic acid derivatives 1 and thionyl chloride has been investigated in detail. Contrary to popular belief the straightforward formation of the corresponding alpha-chloro sulfenyl chlorides 2 is the exception rather than the rule. The propanediamide 2e, not available by the "standard" reaction of le with thionyl chloride, is surprisingly formed by reaction of le with sulfur dichloride. The usefulness of 2 as thiosulfine 4 precursors has been demonstrated.

M3 - Journal article

SN - 1434-193X

VL - 13

SP - 2039

EP - 2045

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

New contributions to the chemistry of 2-chloro-2-(chlorothio)propanedioic diesters and diamides

Abstract

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