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https://hdl.handle.net/2440/17964
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Type: | Journal article |
Title: | The formation of RCCCO and CCC(O)R (R = Me, Ph) neutral radicals from ionic precursors in the gas phase: the rearrangement of CCC(O)Ph |
Author: | Peppe, S. Mc Anoy, A. Dua, S. Bowie, J. |
Citation: | Rapid Communications in Mass Spectrometry, 2004; 18(10):1008-1016 |
Publisher: | John Wiley & Sons Ltd |
Issue Date: | 2004 |
ISSN: | 0951-4198 1097-0231 |
Statement of Responsibility: | Salvatore Peppe, Andrew M. McAnoy, Suresh Dua, John H. Bowie |
Abstract: | Neutrals MeCCCO, CCC(O)Me, PhCCCO and CCC(O)Ph have been made by neutralisation of [MeCCCO](+), [CCC(O)Me](-), [PhCCCO](+) and [CC(CO)Ph](-). Neutrals MeCCCO, CCC(O)Me and PhCCCO are stable for the microsecond duration of the neutralisation experiment. A joint experimental and theoretical study (energies calculated at the B3LYP/aug-cc-pVDZ//B3LYP/6-31G(d) level of theory) suggests that the neutral radical CCC(O)Ph rearranges via a four-centred ipso radical cyclisation/ring opening to form the isomer PhCCCO in an exothermic reaction. (13)C labelling confirms that the rearrangement does not involve O migration. Some of the PhCCCO radicals formed in this reaction are sufficiently energised to effect decomposition to give PhCC and CO. |
Description: | The definitive version may be found at www.wiley.com |
Provenance: | Published Online: 8 Apr 2004 |
DOI: | 10.1002/rcm.1425 |
Published version: | http://dx.doi.org/10.1002/rcm.1425 |
Appears in Collections: | Aurora harvest 6 Chemistry publications |
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