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The Interconversion of cis and trans Isomers Cllnord J. McGlnn and Wllllam B. Wheatley LeMoyne College. Syracuse. NY 13214
I t has long been known that alkenes can be converted t o alkene oxides by the action of peroxyacids,
and that the reaction is stereospecific. I t has also been known since 195g1 that trans-alkene oxides on treatment with tributylphosphine are converted to the cis-alkenes.
The reaction is classified as a Wittig reaction. By the same two reactions i t is possible to convert cis-alkenes into transalkenes. One would certainly expect both reactions to be found in the more commonly used organic texts. However, only the first is found. The only advanced text t o list both reactions is March's Advanced Organic Chemistryz. I t is hoped that for the sake of students both reactions will occur together in future organic texts.
' Boskin, M. J.; Denny, D. B. Chem. Ind. (London) 1959,330-331. March. J. AdvancedOraanic Chemlstw, 3rd ed.; Wiley: New Yo*.
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Journal of Chemical Education
