[2 + 1] cycloaddition reaction of dialkylthioketenes with carbenes - Isomerization of the resulting alkylidenethiiranes

verfasst von

Helmut Behr, Oliver Bolte, Gerald Dräger, Monika Ries, Ernst Schaumann

Abstract

Carbenes generated by metal-catalyzed decomposition of diazo compounds 2 undergo a smooth cycloaddition to the C=S bond of thioketenes 1; products 3 were characterized by spectroscopic means as well as an X-ray structural investigation of 3b. However, photolytic generation of diphenylcarbene from diphenylketene led to an isomeric alkylidenethiirane 4a in the reaction with di-tert-butylthioketene (1a). Analogously, alkylidenethiiranes 3a, b, d, g, h could be photoisomerized to isomers 4a, b, d, g, h. The corresponding rearrangement of S-oxides 8 afforded isomers 9.

Organisationseinheit(en)

Institut für Organische Chemie

Externe Organisation(en)

Universität Hamburg
Technische Universität Clausthal

Typ

Artikel

Journal

Liebigs Annales

Seiten

1295-1299

Anzahl der Seiten

5

ISSN

0947-3440

Publikationsdatum

08.1996

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Allgemeine Chemie

Elektronische Version(en)

https://doi.org/10.1002/jlac.199619960809 (Zugang: Unbekannt)