This work describes the stereochemistry and the relative rates of epoxidation reactions of the title compounds with sulfur ylides (methylenedimethylsulfurane and methylenedimethyloxysulfurane) in DMSO and C6H6. The electronic perturbative effect of substituent X depends on the solvent and on the reactant. It is transmitted in opposite way in solvents of different polarity depending on the reactant. The electronegativity of the substituent scarcely affects the percentages of axial/equatorial attack. The percentage of equatorial attack with methylenedimethyloxysulfurane is markedly lower for 5-X-adamantan-2-ones than for 4-X-cyclohexanones. © 2005 The Japan Institute of Heterocyclic Chemistry All rights reserved
Catanoso, G., Di Credico, B., Vecchi, E. (2005). Sulfur ylides in reactions with 5-X-adamantan-2-ones. Stereochemistry and reactivity. HETEROCYCLES, 65(9), 2151-2160 [10.3987/COM-05-10489].
Sulfur ylides in reactions with 5-X-adamantan-2-ones. Stereochemistry and reactivity
Di Credico, B;
2005
Abstract
This work describes the stereochemistry and the relative rates of epoxidation reactions of the title compounds with sulfur ylides (methylenedimethylsulfurane and methylenedimethyloxysulfurane) in DMSO and C6H6. The electronic perturbative effect of substituent X depends on the solvent and on the reactant. It is transmitted in opposite way in solvents of different polarity depending on the reactant. The electronegativity of the substituent scarcely affects the percentages of axial/equatorial attack. The percentage of equatorial attack with methylenedimethyloxysulfurane is markedly lower for 5-X-adamantan-2-ones than for 4-X-cyclohexanones. © 2005 The Japan Institute of Heterocyclic Chemistry All rights reserved
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