Snider, Barry B.; Vo, Nha Huu; Foxman, Bruce M. published the artcile< Manganese(III)-based oxidative fragmentation-cyclization reactions of unsaturated cyclobutanols>, Synthetic Route of 112-63-0, the main research area is oxidative fragmentation cyclization unsaturated cyclobutanol; manganese acetate oxidation unsaturated cyclobutanol.
Allylic cyclobutanols, e.g., I, are oxidatively fragmented by Mn(OAc)3.2H2O in EtOH to give tertiary radicals. These tertiary radicals undergo both 6-endo-cyclization to the α,β-unsaturated ketone to afford α-keto radicals, and 5-exo-cyclization to provide β-keto cyclopentylmethyl radicals. The α-keto radicals produced by 6-endo-cyclization are reduced to ketones or dimerize. The β-keto radicals formed by 5-exo-cyclization are oxidized by Cu(OAc)2 to yield methylenecyclopentanones and rearrange to give 3-oxocyclohexyl radicals that are oxidized by Cu(OAc)2 to afford cyclohexenones. Thus, oxidation of I with 2 equiv Mn(OAc)3.2H2O and 1 equiv Cu(OAc)2 in EtOH for 1 h at reflux affords 22% methylenecyclopentanone II, 1.5% cyclohexenone III, and 44% tricyclic enone IV. Acetylenic cyclobutanols are oxidatively fragmented by Mn(OAc)3.2H2O in EtOH to provide tertiary radicals that cyclize to give α-keto vinyl radicals, which abstract a hydrogen atom to yield methylenecyclopentanones. Pentenylcyclobutanol V is oxidatively fragmented by Mn(OAc)3.2H2O to afford a tertiary radical which cyclizes to furnish cyclopentylmethyl radicals, which are oxidized by Cu(OAc)2 to methylenecyclopentane VI and an isomer.
Journal of Organic Chemistry published new progress about Cyclization. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Synthetic Route of 112-63-0.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics