Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction

The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of -vinyl phosphorodithioate with thiotosylates or -vinyl...

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Bibliographic Details
Published inMaterials Vol. 14; no. 6; p. 1342
Main Authors Jędrzejewski, Bartosz, Musiejuk, Mateusz, Doroszuk, Justyna, Witt, Dariusz
Format Journal Article
LanguageEnglish
Published Switzerland MDPI 10.03.2021
MDPI AG
Subjects
alkenes
Communication
cycloaddition
hetero-Diels-Alder
thiosulfonates
vinyl disulfides
cycloaddition
thiosulfonates
hetero-Diels-Alder
alkenes
vinyl disulfides
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Summary:The simple, convenient, and efficient methods for the preparation of unsymmetrical vinyl disulfides with additional functional groups under mild conditions with moderate to high yields were designed. The developed methods include the reaction of -vinyl phosphorodithioate with thiotosylates or -vinyl thiotosylate with thiols. The designed methods allow for the synthesis of unsymmetrical vinyl disulfides with additional functionalities such as hydroxy, carboxy, protected amino, or ester groups. Vinyl disulfides reacted with the generated transient -iminothioquinones in an inverse electron-demand [4+2] cycloaddition to produce benzo[ ][1,4]thiazine derivatives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70th anniversary.
ISSN:1996-1944
1996-1944
DOI:10.3390/ma14061342