Riley Oxidation

Riley Oxidation

FollowFollowFollow Riley Oxidation The Riley oxidation is the selenium dioxide-mediated oxidation of methylene groups to alpha ketones and at the allylic position of olefins. Riley Oxidation Reaction Mechanism The oxidation begins with attack by the enol tautomer at...
Reformatsky Reaction

Reformatsky Reaction

FollowFollowFollow Reformatsky Reaction The Reformatsky reaction is the zinc-induced reaction between alpha-halo esters and aldehydes or ketones. Also, a metal-induced reaction of alpha-carbonyl halides with a wide range of electrophiles. General features: 1. The...
Pinacol Rearrangement

Pinacol Rearrangement

FollowFollowFollow Pinacol Rearrangement The Pinacol rearrangement is the acid-catalyzed transformation of vicinal diols to afford ketones or aldehydes. Besides protic acids (H2SO4, HClO4, TsOH), Lewis acids (BF3·OEt2, TMSOTf) are also used. General features: 1....
Pictet-Spengler Reaction

Pictet-Spengler Reaction

FollowFollowFollow Pictet-Spengler Reaction The Pictet-Spengler reaction is the condensation of an arylethylamine with a carbonyl compound in the presence of a protic or Lewis acid to give rise to a substituted tetrahydroisoquinoline. Pictet-Spengler Reaction Reaction...
Parikh-Doering Oxidation

Parikh-Doering Oxidation

FollowFollowFollow Parikh-Doering Oxidation The Parikh-Doering reaction is the oxidation of primary and secondary alcohols into aldehydes and ketones. The procedure uses dimethyl sulfoxide (DMSO) as the oxidant, activated by the sulfur trioxide pyridine complex in the...
Overman Rearrangement

Overman Rearrangement

FollowFollowFollow Overman Rearrangement The Overman rearrangement is the diastereoselective [3,3]-sigmatropic rearrangement of allylic alcohols to give allylic trichloroacetamides through an imidate intermediate. Similar to the mechanism of the Claisen rearrangement,...