1,2-Mercapto alcohols and 1,2-mercapto amines proved to be useful reagents towards Michael acceptors, such as a,b-ethylenic ketones, esters and nitriles leading to variously polyfunctionalized unsymmetric sulfides. Reaction of 1,2-mercapto alcohols with electron-deficient alkynes allowed to obtain b-hydroxy vinyl sulfides as valuable precursors of 1,3-oxathiolane derivatives. Extension to b-hydroxy selenols resulted in the isolation of unsymmetric selenides, formed through a Se-alkylation.
Thio- and Seleno-Michael addition: An efficient tool for the delivery of sulfur and selenium functionalities / Tanini D.; Ermini E.; Capperucci A.. - In: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS. - ISSN 1042-6507. - ELETTRONICO. - 194:(2019), pp. 720-722. [10.1080/10426507.2019.1603229]
Thio- and Seleno-Michael addition: An efficient tool for the delivery of sulfur and selenium functionalities
Tanini D.Membro del Collaboration Group
;Capperucci A.
2019
Abstract
1,2-Mercapto alcohols and 1,2-mercapto amines proved to be useful reagents towards Michael acceptors, such as a,b-ethylenic ketones, esters and nitriles leading to variously polyfunctionalized unsymmetric sulfides. Reaction of 1,2-mercapto alcohols with electron-deficient alkynes allowed to obtain b-hydroxy vinyl sulfides as valuable precursors of 1,3-oxathiolane derivatives. Extension to b-hydroxy selenols resulted in the isolation of unsymmetric selenides, formed through a Se-alkylation.
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