Tetrasubstituted Oxathioles and Olefines Obtained by Cycloaddition of 2-Diazo-1,3-dicarbonyl Compounds to Aliphatic Thiones

Переведенное название: Tetrasubstituted Oxathioles and Olefines Obtained by Cycloaddition of 2-Diazo-1,3-dicarbonyl Compounds to Aliphatic Thiones

A.V. Ivanov, G. Mlosto, V.A. Nikolaev

Результат исследований: Научные публикации в периодических изданияхКраткий обзор

1 Цитирования (Scopus)

Аннотация

Relatively inert diazodiketones react with aliphatic thiones in a way similar to the reaction with aromatic thioketones to produce the corresponding spirocyclic oxathioles. The most probable reaction mechanism involves cycloaddition of the dipolar diazo group to the C=S bond of thione, followed by 1,5-electrocyclization of intermediate C=S ylides. Dimethyl diazomalonate reacts in this way at 19–23°C, whereas at elevated temperatures 1,3-electrocycli-zation of C=S ylide and subsequent desulfurization of thiirane lead to tetrasubstituted olefins as final products.
Переведенное названиеTetrasubstituted Oxathioles and Olefines Obtained by Cycloaddition of 2-Diazo-1,3-dicarbonyl Compounds to Aliphatic Thiones
Язык оригиналаанглийский
Страницы (с-по)1080–1082
ЖурналRussian Journal of Organic Chemistry
Том49
Номер выпуска7
DOI
СостояниеОпубликовано - 2013

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