111. 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 [Rh^ICl(PPh₃)₃]/cumene hydroperoxide resulted in a 1: 1 mixture of (Z)- and (E)-4, while reaction of (Z)-3 with [Fe^III(tpp)]Cl/PhIO gave only (Z)-4 (tpp = tetraphenylporphyrin).

DOI : 10.1002/hlca.19920750310 

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