The Hive > Novel Discourse

New method for P2P

<< < (8/8)

moo:
Good to know. I tried to find out about that a few months ago, but then forgot about it.

Rhodium:
Here is the article I mentioned in Post 503547 (Rhodium: "Baeyer-Villiger on unsaturated ketones", Novel Discourse)

Reaction of ?,?-unsaturated aldehydes with hydrogen peroxide catalysed by benzeneseleninic acids and their precursors
Ludwik Syper
Tetrahedron 43(12), 2853-2871 (1987) (https://www.thevespiary.org/rhodium/Rhodium/pdf/baeyer-villiger.selenium-h2o2.pdf)
DOI:10.1016/S0040-4020(01)86890-3

Abstract
Oxidation of ?,?-unsaturated aldehydes with hydrogen peroxide catalysed by benzeneseleninic acids and their precursors has been investigated. Bis 2-nitrophenyl diselenide has proved to be the most effective catalyst. The major products resulting from the oxidation are vinyl formates (a) which on hydrolysis give saturated aldehydes or ketones (g) having the carbon chain shortened by one carbon atom, compared with the starting aldehydes. The minor products are formyloxyoxiranes (b), ?-hydroxy-carbonyl (e) and ?-formyloxycarbonyl (f) compounds with the carbon chain shortened by one carbon atom. Carbonyl compounds (d), formally derived from an oxidative fission of the carbon-carbon double bond, have been also isolated. Diformyloxy (4c) and formyloxyacetoxy phenylmethane (5c) have been isolated when cinnamaldehyde (4) or 1-phenyl-2-formyloxypropane (5a) were oxidized, respectively. Possible mechanisms of formation of these products are discussed. Similar products resulted when ?,?-unsaturated aldehydes were oxidized with organic peroxyacids.

carl:
Apparently, orthoboric acid can substitute the HCl in the condensation step between MEK and benzaldehyde.
Don't ask me for a reference though, it was told me from a first-hands experience.

Navigation

[0] Message Index

[*] Previous page

Go to full version