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Two-atom azirine ring expansion reaction of methyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate via a dirhodium tetraacetate-catalyzed Wolff rearrangement

Николай В. Ростовский, Михаил С. Новиков, Александр Ф. Хлебников, Дмитрий С. Юфит
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Abstract


Rh2(OAc)4-catalyzed Wolff rearrangement of methyl 2-diazo-3(4-methoxyphenyl)-3-oxopropanoate gave methoxycarbonyl(4-methoxyphenyl)ketene that was added to 2Н-azirines, resulting in opening of the three-membered ring at the N–C(2) bond and leading to the formation of 3,4-dihydro-2Н-pyrrol-2-one derivatives. Depending on the structure of the obtained products, they isomerized to the more stable 1Н-pyrrol-2(3H)-one derivatives or added a water molecule at the C=N bond.


Keywords


2Н-azirines; carbenoids; diazo compounds; ketenes; pyrrolinones; catalysis; Wolff rearrangement

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