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Selenobenzophenones and Diazoalkanes: Isolation of Tetraarylethylenes by the Reaction of Benzophenone Hydrazones with Diselenium Dibromide
Author(s) -
Okuma Kentaro,
Kojima Kazuki,
Oyama Kosuke,
Kubo Kento,
Shioji Kosei
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300510
Subject(s) - benzophenone , chemistry , diazomethane , reaction conditions , hydrazone , ketone , medicinal chemistry , organic chemistry , catalysis
The reaction of selenobenzophenones with diazomethane afforded the corresponding diarylethylenes and symmetrical olefins. The reaction with diaryldiazomethanes gave three different types of tetraarylethylenes. This reaction proceeded through 1,3,4‐selenadiazoline intermediates, and retrocyclization was observed. The formation of 1,3,4‐selendiazolines was independently confirmed by the reaction of benzophenone hydrazones with diselenium dibromide, which afforded tetraarylethylenes in good yields. This method is applicable to the two‐step synthesis of tetraarylethylenes from benzophenones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)