Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/4720
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Type: Journal article
Title: The mechanism of methanol loss from the (M-H)⁻ ions of cis- and trans-4-methoxycyclohexanol. The application of experiment and theory in concert
Other Titles: The mechanism of methanol loss from the (M-H)(-) ions of cis- and trans-4-methoxycyclohexanol. The application of experiment and theory in concert
Author: Bowie, J.
Dua, S.
Raftery, M.
Buntine, M.
Eichinger, P.
Citation: Journal of the Chemical Society. Perkin transactions II, 1996; 1(11):2489-2496
Publisher: Royal Society of Chemistry
Issue Date: 1996
ISSN: 1472-779X
1364-5471
Statement of
Responsibility: 
Suresh Dua, Mark A. Buntine, Mark J. Raftery, Peter C. H. Eichinger and John H. Bowie
Abstract: Deprotonation of cis- and trans-4-methoxycyclohexanol by HO– in the ion source of a mass spectrometer yields the (M – H)– alkoxide ions exclusively. Both of these ions, on collisional activation, form MeO–, MeO–(H2O) and eliminate MeOH. The loss of methanol forms the base peak of the spectrum, and the structure of this daughter anion is shown to be the alkoxide ion from cyclohex-3-enol for both isomers. Evidence (based on product ion, deuterium labelling and AM1 semiempirical computational studies) indicates that the loss of methanol from the trans isomer proceeds by an internal SN2 cyclisation of O– at the four position (through a 1,4-epoxycyclohexane species) followed by 3,4 elimination. A similar sequence may occur for the cis-isomer, but in this case the process is not as energetically favourable as that for the trans isomer.
Rights: Copyright status unknown
RMID: 0030002736
DOI: 10.1039/P29960002489
Appears in Collections:Chemistry publications

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