Revision as of 13:46, 24 June 2020 edit Smokefoot (talk \| contribs) Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers 78,479 edits of course the title is a misnomer ← Previous edit		Revision as of 13:49, 24 June 2020 edit undo Smokefoot (talk \| contribs) Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers 78,479 edits →Mechanism and stereochemistry: more clear Next edit →
Line 16: ==Mechanism and stereochemistry== [[Chromate ester]]s are implicated in these reactions. The chromate ester decompose to the aldehyde or carbonyl by transfer of a proton alpha to the hydroxy group. Large kinetic isotope effects are observed.<ref>Banerji, K. K. ''J. Org. Chem.'', '''1988''', ''53'', 2154.</ref> ~~===Prevailing mechanisms===~~ Chromate esters have been implicated in most oxidations of alcohols by chromium(VI)-amines. Upon formation of the chromate ester, either deprotonation or hydride transfer leads to the product carbonyl compound. Kinetic isotope effect studies have shown that C-H bond cleavage is involved in the rate-determining step.<ref>Banerji, K. K. ''J. Org. Chem.'', '''1988''', ''53'', 2154.</ref> <span style="float:right;padding-right:50px;padding-top:30px;">'''''(2)'''''</span><center>[[File:ChroMech1.png]]</center> Oxidative annulation of alkenols to form six-membered rings may be accomplished with PCC. This process is postulated to occur via initial oxidation of the alcohol, attack of the alkene on the new carbonyl, then re-oxidation to a ketone. Double-bond isomerization may occur upon treatment with base as shown in equation (3) below.<ref>Corey, E. J.; Boger, D. ''Tetrahedron Lett.'', '''1978''', ''19'', 2461.</ref>

Oxidation with chromium(VI) complexes: Difference between revisions