INVESTIGADORES
GARAY Raul Oscar
artículos
Título:
Methoxide-induced Fragmentation of 2,2,3-Trihalogeno- and 2,2-Dihalogeno-3-methoxy-1,3-diphenylpropanoates
Autor/es:
MONTANI, R. S.; GARAY, R. O.; CABALEIRO, M. C.
Revista:
JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS 2 (2001)
Editorial:
RSC
Referencias:
Lugar: Londres; Año: 1989 p. 1125 - 1130
ISSN:
1472-779X
Resumen:
The reaction of
2,2,3-trihalogeno-1,3-diphenylpropanones with sodium methoxide in methanol
occurs with exclusive formation of fragmentation products. Kinetic and
stereochemical evidence is interpreted in terms of a concerted intramolecular
process promoted by initial attack of methoxide anion at the carbonyl carbon.
In the case of 2,2-dihalogeno-3-methoxy-1,3-diphenylpropanones the reaction
gives fragmentation, rearrangement, and elimination products. The former
products are believed to be formed through competing reactions involving an
intermediate formed on addition of methoxide to the substrate. For the
fragmentation pathway the results are consistent with a
carbanionic-intermediate mechanism.