IQUIR   05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
Assessing the halogen effect in Diels-Alder reactions involving chiral a-halo enones on the basis of a combined experimental and DFT computational approach
Autor/es:
SAROTTI, ARIEL M.; SPANEVELLO, ROLANDO A.; SUÁREZ, ALEJANDRA G.
Revista:
TETRAHEDRON LETTERS
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Lugar: Amsterdam; Año: 2011 vol. 52 p. 4145 - 4148
ISSN:
0040-4039
Resumen:
An experimental and computational study was conducted to assess the effect of chlorine and bromine substitution in Diels–Alder reactions involving chiral a-halo enones as dienophiles. An important rate  enhancement was observed in the case of acyclic dienes, while the use of cyclic dienes resulted in prolonged reaction times and lower yields. DFT calculations suggest that these reactions are governed by finely balanced geometric and electronic features at the TSs.