ORGLIST: Olefinic oxidation and cleavage

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From: Badru Nsubuga (bdnsubuga$##$yahoo.co.uk)
Date: Thu Sep 20 2001 - 11:38:49 EDT




In oak wood chemistry as it relates to
aging/maturation of distilled beverages, several
authors mention the conversion of cinnamaldehyde to
benzaldehyde . They insist that the conversion
involves the breaking of the olefinic bond and
oxygenation. Is that alpha-beta cleavage common? Any
organic chem literature?

What is the mechanism? Any free radical involved?

For the past six months, my attempts to convert
coniferaldehyde to vanillin and sinapaldehyde to
syringaldehyde using oxygen and heat have not been
successful. The attempts resulted in the purification
of the starting materials through sublimation!

Any assistance would be greatly appreciated.

B. Nsubuga

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