Opening oxidative rearrangement

Addition of isopropyl lithium to the surviving ketone followed by oxidative rearrangement of the resulting tertiary ailylic alcohol and concomitant oxidation of the secondary allylic alcohol gave the diketone 10. Selective addition of methyl lithium to the less hindered of the two ketones, again from the more open face, then gave 3. 

Aqueous permanganate converts l,3-dibenzyl-2-phenylimidazolidine into a mixture of benzamide and benzoic acid. When l-alkyl-3-phenylimidazolidines are subjected to N-oxidation the unstable JV-oxides rearrange to give tetrahydro-l,2,5-oxadiazines (180) via the ring-opened product (Scheme 89) (77LA956). 

Reactions of arene oxides ring opening and rearrangement (Section 12.8). 

Oxidative rearrangement and ring expansion of strained molecules of tert-cyclo-butanols are known [206]. Recently it has been claimed that the reaction can be explained more reasonably by elimination of jS-carbon (see Chapter 3.8.2) [207]. Conversion of the vinylcyclobutanol 490 to the ring-opened product 493 by relief of the ring strain under oxidative conditions is explained by j6-carbon elimination as shown by 491 to generate 492, followed by j6-H elimination. In this ease. 

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