91256-86-9Relevant academic research and scientific papers
CHEMISTRY OF ENOL ETHERS. LXVII. STEREOCHEMISTRY OF THE ADDITION OF ACETALS TO THE CIS AND TRANS ISOMERS OF β-BROMOVINYL METHYL ETHER
Raifel'd, Yu. E.,Arshava, B. M.,Morozhenko, Yu. V.,Slonim, I. Ya.,Makin, S. M.
, p. 231 - 236 (2007/10/02)
The condensation of the acetals of unsaturated, α,β-unsaturated, and aromatic aldehydes with the cis and trans isomers of β-bromovinyl methyl ether in the presence of boron trifluoride etherate as catalyst is stereospecific.The erythro isomers of the α-bromo-β-alkoxy acetals are formed in the reaction with trans-β-bromovinyl methyl ether.The electronic effects of the substituent in the acetal do not have an appreciable effect on the stereochemistry of condensation, which is controlled to a greater degree by steric factors.The configurations of the erythro andthreo isomers of the α-bromo-β-alkoxy acetals were determined by means of the PMR and 13C NMR spectra.
