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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
Statement of
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
Provenance: Published Online: 8 Apr 2004
RMID: 0020040485
DOI: 10.1002/rcm.1425
Appears in Collections:Chemistry publications

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