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|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|
Mc Anoy, A.
|Citation:||Rapid Communications in Mass Spectrometry, 2004; 18(10):1008-1016|
|Publisher:||John Wiley & Sons Ltd|
|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|
|Appears in Collections:||Chemistry publications|
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