Zhenfeng Xi and co-workers from SIOC have reported in ACIE on the transfer of a halogen from an aryl group to an alkyl group.
Posted by naturalproductman on August 28, 2014
Petr Beier and co-workers from the Academy of the Sciences of the Czech Republic have reported in JOC on an interesting reaction involving hydrogen peroxide, and an SF5-phenol to afford a muconolactone derivative.
Posted by naturalproductman on July 27, 2014
Paul Hergenrother and co-workers from UIUC have reported in ACIE on an interesting rearrangement to form fenestrane ring systems.
Posted by naturalproductman on June 30, 2014
James Leighton and co-workers reported in JACS on a mechanistic study of a tandem Ireland Claisen/Cope rearrangement reaction to form some polycyclic rings.
Posted by naturalproductman on May 14, 2014
Cristina de Meo and co-workers from Southern Illinois University reported in Organic Letters on a thiosialoside elimination of a thiophenol group, occuring by syn-elimination.
Posted by naturalproductman on May 7, 2014
Marco Fraaije and co-workers from the University of Groningen in the Netherlands have reported in ACIE on an enzyme catalyzed oxidation of an alcohol to carboxylic acid.
They did a mechanistic study, which caught my attention. They wanted to test if the carboxylic acid arises from the gem-diol of the aldehyde intermediate or directly from the aldehyde. The experiment was run under 18O-labeled water with 4-nitrobenzaldehyde. They state that if the reaction is spontaneous then the aldehyde will directly give the carboxylic acid with no 18O incorporated in the product, but if it is from the gem-diol, you will have 18O-atoms.
I have a problem with this part because the reaction can still come from the aldehyde if the carboxylic acid had an 18O-atom. The way this would occur is that the aldehyde can get hydrated to the gem-diol then it would be in equilibrium with the aldehyde and give back the aldehyde but this time it has an 18O-atom (STEP 2 product of below). This aldehyde, if oxidized by the enzyme, would yield the carboxylic acid with 18O-atom.
Anyway, interesting paper.
Posted by naturalproductman on May 7, 2013
Pierre Yves-Renard and co-workers from CNRS have reported in Organic Letters on an interesting synthesis of pyridines.