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- W2952663399 abstract "The epoxidation reactions of a series of cis-3,4-disustituted-(CH2X)-cyclobutenes 1–8 with dimethyldioxirane (DMD) and mClPBA have been investigated with both reagents. A remarkable syn diastereoselectivity in the formation of the epoxide has been observed for substrates bearing electron withdrawing substituents. Transition structures for epoxidations of 3,4-dimethylcyclobutene (1), diastereoisomeric 3,5-dioxa-4-thia-bicyclo[5.2.0]non-8-ene-4-oxides 7 and 8, and 3,4-bis(mesyloxymethyl)-1-cyclobutene (5) with dioxirane and peroxyformic acid have been located with the B3LYP/6–31G∗ method. Experimental dominant syn facial selectivity is rationalized mostly as a result of an electrostatic attractive interaction involving the peroxo oxygens of the oxidizing reagents and the positively charged homoallylic hydrogens of the olefins." @default.
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- W2952663399 title "Stereoselective epoxidation of cis-3,4-disubstituted-(CH2X)-cyclobutenes with dimethyldioxirane and peroxy acids. Experimental and computational evidence for a syn-orienting electrostatic effect" @default.
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- W2952663399 doi "https://doi.org/10.1016/s0040-4020(99)00630-4" @default.
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