TY - JOUR
T1 - Substituent effects on the reaction mode between 2-hydroxybenzyl alcohol derivatives and MEM chloride:synthesis and mechanistic aspects of seven-and ten-membered benzo-fused O,O-acetals
AU - Aiello, Stefania
AU - Díaz-Gavilán, Mónica
AU - Gallo, Miguel Á.
AU - Saniger, Estrella
AU - Choquesillo, Duane
AU - González-Pérez, Josefa M.
AU - Espinosa, Antonio
AU - Aiello, Stefania
AU - Campos, Joaquín M.
AU - Delgado, Beatriz
PY - 2004
Y1 - 2004
N2 - The synthesis of (RS)-2- or (RS)-3-methoxy-2,3-dihydro-5H-1,4-benzodioxepins and (RS)-5- or (RS)-3-methoxy-2,3,5,6-tetrahydro-8H-benzo-[1,4,7]-trioxecins has been developed. The mechanism of such a reaction via the boron trifluoride etherate-promoted transformation of 2-(methoxyethoxymethoxy)benzyloxyacetaldehyde dimethyl acetals or 2-(methoxyethoxymethoxymethyl)phenyloxyacetaldehyde dimethyl acetals has been proposed. Transannular versions of the reaction results in the facile ring contraction of 12-membered intermediates to the 10- and to 7-membered benzene-fused O,O-acetals. The characterization of the by-products strongly supports the mechanisms proposed.
AB - The synthesis of (RS)-2- or (RS)-3-methoxy-2,3-dihydro-5H-1,4-benzodioxepins and (RS)-5- or (RS)-3-methoxy-2,3,5,6-tetrahydro-8H-benzo-[1,4,7]-trioxecins has been developed. The mechanism of such a reaction via the boron trifluoride etherate-promoted transformation of 2-(methoxyethoxymethoxy)benzyloxyacetaldehyde dimethyl acetals or 2-(methoxyethoxymethoxymethyl)phenyloxyacetaldehyde dimethyl acetals has been proposed. Transannular versions of the reaction results in the facile ring contraction of 12-membered intermediates to the 10- and to 7-membered benzene-fused O,O-acetals. The characterization of the by-products strongly supports the mechanisms proposed.
UR - http://hdl.handle.net/10447/19411
M3 - Article
VL - 60
SP - 11453
EP - 11464
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
ER -