Reaction of ketone hydrazones with diselenium dihalides: Simple synthesis of Delta(3)-1,3,4-selenadiazolines and 2,5-diarylselenophenes

Sterically congested cis- and trans-Delta(3)-1,3,4-selenadiazolines were isolated by one-pot reactions of ketone hydrazones with diselenium dibromide, which suggested the in situ formation of selone and diazoalkane intermediates. The thermolysis of these compounds gave symmetrical olefins, whereas o...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 78; no. 6; pp. 1121 - 1126
Main Authors Okuma, K, Izaki, T, Kubo, K, Shioji, K, Yokomori, Y
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 15.06.2005
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
TELLURIUM
STEREOCHEMISTRY
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Summary:Sterically congested cis- and trans-Delta(3)-1,3,4-selenadiazolines were isolated by one-pot reactions of ketone hydrazones with diselenium dibromide, which suggested the in situ formation of selone and diazoalkane intermediates. The thermolysis of these compounds gave symmetrical olefins, whereas oxidation afforded the corresponding azines. The reaction of acetophenone hydrazones with diselenium dibromide afforded 2,5-diarylselenophenes in moderate yields. The reaction proceeded through selone intermediates.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.78.1121