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

Stefania Aiello, Mónica Díaz-Gavilán, Miguel Á. Gallo, Estrella Saniger, Duane Choquesillo, Josefa M. González-Pérez, Antonio Espinosa, Stefania Aiello, Joaquín M. Campos, Beatriz Delgado

Risultato della ricerca: Article

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Abstract

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.
Lingua originaleEnglish
pagine (da-a)11453-11464
Numero di pagine12
RivistaTetrahedron
Volume60
Stato di pubblicazionePublished - 2004

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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Aiello, S., Díaz-Gavilán, M., Gallo, M. Á., Saniger, E., Choquesillo, D., González-Pérez, J. M., Espinosa, A., Aiello, S., Campos, J. M., & Delgado, B. (2004). 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. Tetrahedron, 60, 11453-11464.