QUINONE METHIDE MEDIATED OXIDATION REACTION: OXIDATIVE CLEAVAGE OF CARBON-CARBON BOND IN 2-(3, 5-DI-TERTBUTYL-4-HYDROXYPHENYL)METHYL PROPAN-1-ONE OXIMS USING DDQ

Novel 2-(3, 5-Di-tert-Bu-4-hydroxyphenyl)methyl propan-1-one oxime derivatives were prepared. Treatment of 2-(3, 5-Di-tert-Bu-4-hydroxyphenyl)methyl propan-1-one oximes with DDQ inwet CH2Cl2 leads to oxidative C-C cleavage giving rise to mixtures 4-hydroxy-3, 5-Di-tert-butyl benzaldehyde and constituent oximes. This reaction proceeds via formation of p-quinone methide as transition intermediate

Keywords:

Quinone methide , Oxime , Oxidation , DDQ