91253-93-9Relevant academic research and scientific papers
Conformational and steric effects on regioselectivity in the Baeyer-Villiger reaction
Dave, Vinod,Stothers, J. B.,Warnhoff, E. W.
, p. 1965 - 1970 (2007/10/02)
The Bayer-Villiger oxidation of six β,β,γ-trisubstituted cyclopentanones and cyclohexanones leads to preferential migration of the α-carbon relative to the α'-carbon by a factor of 1.5-4:1.The origin of the preference is suggested to be steric and is ascribed to the greater relief of non-bonded interactions as the α-β bond lengthens in going to the transition state.Thus, in the carbonyl addition intermediate the 1,3-diaxial-like interaction between the hydroxyl and the closest γ-carbon is diminished to a greater extent when the α-carbon migrates relative to the α'-carbon.
Sulphur participation in cyclization reactions
Loos, Walter A. J. de,Kuijk, Anne J. W. van den Berg-van,Iersel, Hans M. van,Haan, Jan W. de,Buck, Henk M.
, p. 53 - 57 (2007/10/02)
Cyclization initiated by thiiranium ions was investigated.Cis-fused decalins were formed by a process involving inversion.In nitromethane a sulphonium salt 8 was formed.The reactions of 8 with nucleophilic reagent deviated from those of comparable compoun
