AI Article Synopsis
- Neutrals MeCCCO, CCC(O)Me, and PhCCCO were produced by neutralizing their charged counterparts, and they remain stable for about a microsecond.
- A combined experimental and theoretical investigation reveals that the radical CCC(O)Ph undergoes an exothermic rearrangement through a four-centred reaction, resulting in the formation of isomer PhCCCO.
- Carbon-13 labeling confirms that this rearrangement does not involve oxygen migration and indicates some PhCCCO radicals can decompose to produce PhCC and carbon monoxide (CO).
Article 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.
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| http://dx.doi.org/10.1002/rcm.1425 | DOI Listing |
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