Oxyfunctionalization of Active Methylene Compounds Using Sodium Chlorite in Water

A methylene group inserted between proximal carbonyl groups underwent exclusive oxyfunctionalization with sodium chlorite in the presence of redox-inert Hf-IV in water. Direct oxidation methods have conventionally suffered from manifold side reactions such as oxidative fragmentation, dimerization, a...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 7; no. 2; pp. 350 - 354
Main Authors Kitanosono, Taku, Tani, Shinki, Kobayashi, Shu
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.02.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SELECTIVE OXIDATION
DICARBONYL-COMPOUNDS
1,3-DICARBONYL COMPOUNDS
DIOXIDE
oxidation
FLEXIBACTER SP Q17897
green chemistry
water
TRIOXO COMPOUNDS
COMPLEX-FORMATION
VICINAL TRICARBONYL COMPOUNDS
BETA-DIKETONES
CHEMISTRY
hafnium
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Summary:A methylene group inserted between proximal carbonyl groups underwent exclusive oxyfunctionalization with sodium chlorite in the presence of redox-inert Hf-IV in water. Direct oxidation methods have conventionally suffered from manifold side reactions such as oxidative fragmentation, dimerization, and overreactions, together with the use of toxic and intractable oxidants. Although alternative routes involving prior-functionalization can be executed under mild conditions, preparatively valuable oxidation methods that deliver high levels of both conversion and selectivity remain a prized goal from the standpoint of streamlining organic synthesis. Chlorine dioxide, which was generated as a yellowish gas during the reaction, is considered to be a bona fide oxidant against active methylene compounds. The pivotal role of water was clear, given that the reaction was significantly retarded in both aqueous acetonitrile and ethanol, which can solubilize sodium chlorite.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700646