Mechanism of stereospecific alcohol elimination from cyclohexane trans-1,3-dicarboxylates under electron impact ionization |
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Authors: | A Etinger A Idina A Mandelbaum |
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Abstract: | Diesters of cyclohexane trans-1,3-dicarboxylic acid give rise to major M ? ROH]+·. ions under electron impact ionization. A mass spectral study of the isomeric mixed methyl ethyl esters of the diacid, substituted by a methyl group at position 1 and deuterium labelled at position 3, indicates a stepwise mechanism for this alcohol elimination; the 3-hydrogen (or deuterium) is transferred to the carbonyl of the 1-ester group in the initial step. Subsequent migration of that hydrogen (or deuterium) to the alkoxyl of position 3 results in the highly site- and stereospecific alcohol elimination. CID spectra of the M ? ROH]+. ions obtained from the stereoisomeric diesters clearly show that they have different structures (or are different mixtures of structures). |
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