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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2151-2160
Published online, 26th July, 2005
DOI: 10.3987/COM-05-10489
Sulfur Ylides in Reactions with 5-X-Adamantan-2-ones. Stereochemistry and Reactivity

Giada Catanoso, Barbara Di Credico, and Elisabetta Vecchi*

*Department of Chemistry, C. N. R. Institute of Biomolecular Chemistry - Roma Section, University “La Sapienza”, Piazzale Aldo Moro 5, I-00185 Roma, Box 34 Roma 62, Italy

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.