A convenient method for the preparation of functionalized N-acylsulfenamides from primary amides

We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles ge...

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Bibliographic Details
Published inPhosphorus, sulfur, and silicon and the related elements Vol. 191; no. 2; pp. 305 - 310
Main Authors Musiejuk, Mateusz, Witt, Dariusz
Format Journal Article
LanguageEnglish
Published ABINGDON Taylor & Francis 01.02.2016
Taylor & Francis Ltd
Subjects
amide
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
phosphorodithioic acid
phthalimide
Physical Sciences
Science & Technology
Sulfenamide
thiols
ONE-POT SYNTHESIS
EFFICIENT SYNTHESIS
SYMMETRICAL TRISULFIDES
phthalimide
H-1 ENDOR SPECTRA
SULFUR-NITROGEN
SULFENAMIDE DERIVATIVES
amide
S BOND FORMATION
Sulfenamide
phosphorodithioic acid
UNSYMMETRICAL DISULFIDES
thiols
AMINYL RADICALS
DIARYL DISULFIDES
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Summary:We have developed a convenient method for the synthesis of functionalized N-acylsulfenamides under mild conditions and in moderate to good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with nitrogen nucleophiles generated from primary amides or imides and sodium hydride. The developed method allows for the preparation of N-acylsulfenamides bearing additional hydroxyl, carboxyl, or amino functionalities.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2015.1065258