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

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OriginalspracheEnglisch
Seiten (von - bis)1295-1299
Seitenumfang5
FachzeitschriftLiebigs Annales
Ausgabenummer8
PublikationsstatusVeröffentlicht - 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.

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[2 + 1] cycloaddition reaction of dialkylthioketenes with carbenes - Isomerization of the resulting alkylidenethiiranes. / Behr, Helmut; Bolte, Oliver; Dräger, Gerald et al.
in: Liebigs Annales, Nr. 8, 08.1996, S. 1295-1299.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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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",
author = "Helmut Behr and Oliver Bolte and Gerald Dr{\"a}ger and Monika Ries and Ernst Schaumann",
note = "Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "1996",
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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

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DO - 10.1002/jlac.199619960809

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JO - Liebigs Annales

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