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

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 › peer review

8 Citazioni (Scopus)

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 originale	English
pagine (da-a)	11453-11464
Numero di pagine	12
Rivista	Tetrahedron
Volume	60
Stato di pubblicazione	Published - 2004

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.

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

In: Tetrahedron, Vol. 60, 2004, pag. 11453-11464.

Risultato della ricerca: Article › peer review

Aiello, S, Díaz-Gavilán, M, Gallo, MÁ, Saniger, E, Choquesillo, D, González-Pérez, JM, Espinosa, A, Aiello, S, Campos, JM & 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, vol. 60, pagg. 11453-11464.

Aiello, Stefania ; Díaz-Gavilán, Mónica ; Gallo, Miguel Á. ; Saniger, Estrella ; Choquesillo, Duane ; González-Pérez, Josefa M. ; Espinosa, Antonio ; Aiello, Stefania ; Campos, Joaquín M. ; Delgado, Beatriz. / 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. In: Tetrahedron. 2004 ; Vol. 60. pagg. 11453-11464.

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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.",

author = "Stefania Aiello and M{\'o}nica D{\'i}az-Gavil{\'a}n and Gallo, {Miguel {\'A}.} and Estrella Saniger and Duane Choquesillo and Gonz{\'a}lez-P{\'e}rez, {Josefa M.} and Antonio Espinosa and Stefania Aiello and Campos, {Joaqu{\'i}n M.} and Beatriz Delgado",

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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

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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

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SP - 11453

EP - 11464

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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