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[2 + 1] Cycloaddition Reaction of Dialkylthioketenes with Carbenes - Isomerization of the Resulting Alkylidenethiiranes

✍ Scribed by Behr, Helmut ;Bolte, Oliver ;Dräger, Gerald ;Ries, Monika ;Schaumann, Ernst

Book ID
102905123
Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
501 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

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.

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