Journal of Organic Chemistry p. 5179 - 5182 (1984)
Update date:2022-09-26
Topics:
Mohrig, Jerry R.
Dabora, Sandra L.
Foster, Ted F.
Schultz, Steve C.
Hydrogenation of the methyl esters of (Z)- and (E)-3-(benzoyloxy)-2-butenoate produces reduced products in good yield with highly stereoselective syn additon.Reaction of the alkenes with deuterium is preferable to reaction of the 2-deuterioalkenes with hydrogen.NMR measurements indicated 99.8 percent or greater syn addition of D2 with the Z alkene.Addition of HD to the E alkene produced no regioselectivity, indicating that either the alkylrhodium intermediate forms without kinetic isotope effects or without regioselectivity.
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Doi:10.1039/c39800000126
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