Stereochemical Relationships of the Isomeric 2,3-Butanediols and Related Compounds; Evidence of Walden Inversion

Abstract

This investigation has been undertaken for the purpose of synthesizing cis- and trans-2-butene in a pure state and of studying the Walden inversion. Incidentally, the work has constituted an independent confirmation of the observation that the butene produced in the dehydration of 1-butanol in the presence of sulfuric acid is approximately 68% trans-2-butene and 32% cis-2-butene. The reliability of this result has been questioned, on the basis that the dibromide method of analysis is faulty. This confirmation rests upon the observation that cis-2-butene is converted through the chlorohydrin to cis-2,3-epoxybutane and that the crude epoxybutane mixture obtained from the crude butene mixture is approximately 65% trons-2,3-epoxybutane and 35% cis-2,3-epoxybutane, with little or no 1,2-epoxybutane.

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