Revision as of 08:49, 8 June 2017 edit Double sharp (talk \| contribs) Autopatrolled, Extended confirmed users, Page movers, File movers, Pending changes reviewers 103,194 edits No edit summary ← Previous edit		Revision as of 18:25, 23 October 2019 edit undo 2620:105:b005:100:24b9:fa83:ed44:5dfe (talk) →Prevailing mechanisms Next edit →
Line 11: ==Mechanism and stereochemistry== ===Prevailing mechanisms=== Chromate esters have been implicated in most oxidations of alcohols by chromium(VI)-amines. ~~After~~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