Stereoselective ring-opening reactions with AcBr and AcCl. A new method for preparation of some haloconduritols
Özet
The actions of AcX (X=Br, Cl) on 7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-diol diacetates and a transoid-epoxide prepared from the acetonide of cyclohexa-3,5-diene-cis-1,2-diol were studied. H2SO4-catalyzed cleavage of exo-cis-7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-diol diacetate with AcCl gave (1alpha,2alpha,3alpha,6beta)-6-chloro-4-cyclohexene-1,2,3-triol triacetate, from which the corresponding chloroconduritol was obtained by trans-esterification (MeOH/HCl). A similar reaction of the exo-diacetate with AcBr in the presence of H2SO4 resulted in bromine addition. The formation of bromine from the reaction of AcBr and H2SO4 was observed by independent experiments. H2SO4-catalyzed reaction of etido-cis-7-oxa-bicyclo[2.2.1]hept-5-ene-2,3-diol diacetate with AcX (X=Br, Cl) gave (1alpha,2alpha,3beta,6beta)-6-halo-4-cyclohexene1,2,3-triol triacetates. The reaction of the transoid-epoxide with AcX (X=Br, Cl) with no catalyst gave also (1alpha,2alpha,3beta,6beta)-6-halo-4-cyclohexene-1,2,3-triol triacetates. (C) 2003 Elsevier Ltd. All rights reserved.
Anahtar kelimeler
Atıf için künye
BARAN, A., Kazaz, C., & Seçen, H. (2004). Stereoselective ring-opening reactions with AcBr and AcCl. A new method for preparation of some haloconduritols. TETRAHEDRON, 60(4), 861–866. https://doi.org/10.1016/j.tet.2003.11.054
BibTeX
@article{baran2004-70843,
author = {BARAN, Arif and Kazaz, Cavit and Seçen, Hasan},
title = {Stereoselective ring-opening reactions with AcBr and AcCl. A new method for preparation of some haloconduritols},
journal = {TETRAHEDRON},
year = {2004},
volume = {60},
number = {4},
pages = {861--866},
issn = {0040-4020},
doi = {10.1016/j.tet.2003.11.054},
url = {https://akademik.atauni.edu.tr/yayinlar/70843-stereoselective-ring-opening-reactions-with-acbr-and-accl-a-new-method-for}
}