Effect of excess reactant on the steric course of carbonyl olefination

Bergel'son, L. D.; Vaver, V. A.; Barsukov, L.I.; Shemyakin, M. M.

doi:10.1016/s0040-4039(00)71711-4

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Stereochemistry1

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2009

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Cited by 16 publications

(2 citation statements)

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“…However, no convincing explanation has yet been given for the preferred formation of the less stable erythro-betaines and cis-olefins in the reaction of nonstabilized ylids with aldehydes in nonpolar media. Bergelson, et al (19,22) have attributed the preferred formation of the erythro-betaine to attraction of the carbonyl oxygen to one of the electron-deficient phenyl {ïroups attached to the phosphorus in the ylid. In the transition state li-ad in)*.…”

Section: Stereochemistrymentioning

confidence: 99%

Studies on the mechanism and stereochemistry of phosphonate anion condensations

Mandanas

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Section: Stereochemistrymentioning

confidence: 99%

Studies on the mechanism and stereochemistry of phosphonate anion condensations

Mandanas

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“…Bergelson, et al (18,19) have interpreted their results to Indicate that the rate-determining step is betaine formation, even in the case of nonstabilized ylids.…”

Section: Mechanismmentioning

confidence: 99%