The Dowd-Beckwith ring expansion: a theoretical study |
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| Authors: | Diego Ardura |
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| Institution: | Departamento de Química Física y Analítica, Universidad de Oviedo, C/Julián Clavería, 8, Oviedo 33006, Spain |
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| Abstract: | UB3LYP/6-311++G(d,p) and ROMP2/6-311++G(d,p)//UB3LYP/6-311++G(d,p) calculations including the effect of benzene solvent through the PCM-UAHF method render a concerted mechanism without fragmentation as the most favourable one for the Dowd-Beckwith radical ring expansion of the bromomethyl adduct of methyl cyclopentanone-2-carboxylate to yield methyl cyclohexanone-3-carboxylate. The corresponding concerted TS is a bicyclic alcoxy radical. |
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| Keywords: | Radical ring expansion DFT calculations Dowd-Beckwith reaction |
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