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Publication 111
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P. Müller, J. Pfyffer,
“The Isotopomeric (Z)- and (E)-2,3-Dimethyl(1,1,1,4,4,4-2H6)but-2-enes: Mechanistic Probes for Stereospecific Epoxidation”
Helv. Chim. Acta 1992, 75, 745-750.
By unambiguous methods, (Z)- and (E)-2, 3-dimethyl(1, 1, 1, 4, 4, 4-2H6)but-2-enes (3) were synthesized and transformed to the epoxides 4 with 3-chloroperbenzoic acids. Both the isotopomeric olefins and the epoxides are detected separately by 1H-NMR at 400 MHz. Epoxidation of (Z)-3 with [RhICl(PPh3)3]/cumene hydroperoxide resulted in a 1: 1 mixture of (Z)- and (E)-4, while reaction of (Z)-3 with [FeIII(tpp)]Cl/PhIO gave only (Z)-4 (tpp = tetraphenylporphyrin).
DOI : 10.1002/hlca.19920750310
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