Details
| Original language | English |
|---|---|
| Pages (from-to) | 1295-1299 |
| Number of pages | 5 |
| Journal | Liebigs Annales |
| Issue number | 8 |
| Publication status | Published - Aug 1996 |
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.
Keywords
- Carbenes, Rearrangements, Thiiranes, Thioketenes, [2 + 1] Cycloadditions
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
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In: Liebigs Annales, No. 8, 08.1996, p. 1295-1299.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - [2 + 1] cycloaddition reaction of dialkylthioketenes with carbenes - Isomerization of the resulting alkylidenethiiranes
AU - Behr, Helmut
AU - Bolte, Oliver
AU - Dräger, Gerald
AU - Ries, Monika
AU - Schaumann, Ernst
N1 - Copyright: Copyright 2020 Elsevier B.V., All rights reserved.
PY - 1996/8
Y1 - 1996/8
N2 - 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.
AB - 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.
KW - Carbenes
KW - Rearrangements
KW - Thiiranes
KW - Thioketenes
KW - [2 + 1] Cycloadditions
UR - http://www.scopus.com/inward/record.url?scp=33748985164&partnerID=8YFLogxK
U2 - 10.1002/jlac.199619960809
DO - 10.1002/jlac.199619960809
M3 - Article
AN - SCOPUS:33748985164
SP - 1295
EP - 1299
JO - Liebigs Annales
JF - Liebigs Annales
SN - 0947-3440
IS - 8
ER -