Cleavage of C=N derivatives and oxidation of thiols in water under neutral conditions with 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride

1,4-Diazabicyclo[2,2,2]octane (DABCO) is easily chlorinated and gives a complex which efficiently converts aliphatic and aromatic oximes, phenylhydrazones and semicarbazones to their corresponding carbonyl compounds in water at 50 degrees C in high yield. This reagent can also be used for conversion...

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Bibliographic Details
Published inJournal of chemical research Vol. 2007; no. 8; pp. 486 - 489
Main Authors Tajbakhsh, Mahmood, Habibzadeh, Setareh
Format Journal Article
LanguageEnglish
Published LONDON Sage 01.08.2007
Sage Publications Ltd
Subjects
Aliphatic compounds
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
REAGENT
REGENERATION
deprotection
oxidation
CARBONYL-COMPOUNDS
oximes
DISULFIDES
semicarbazones
DEOXIMATION
MILD
ETHERS
1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride
phenylhydrazones
thiols
EFFICIENT
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Summary:1,4-Diazabicyclo[2,2,2]octane (DABCO) is easily chlorinated and gives a complex which efficiently converts aliphatic and aromatic oximes, phenylhydrazones and semicarbazones to their corresponding carbonyl compounds in water at 50 degrees C in high yield. This reagent can also be used for conversion of thiols to their compounding disulfide under the same reaction conditions. DABCO is quantitatively recovered which can be rechlorinated and reused several times.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:1747-5198
2047-6507
DOI:10.3184/030823407X240890