86324-86-9Relevant academic research and scientific papers
SYNTHESIS OF 2,3-DIHALOGENO-2,3-DIHYDROBENZOFURANS: REGIOSELECTIVITY AND STEREOCHEMISTRY
Perugini, Renzo,Ruzziconi, Renzo,Sebastiani, Giovanni V.
, p. 149 - 152 (2007/10/02)
The synthesis of a series of bromochloro- and chlorofluoro-2,3-dihydrobenzofurans has been carried out.In the bromochlorination of benzofuran trans adducts were obtained and a dependence of the reaction regioselectivity on the solvent polarity and the halogenating species was observed.The reaction of silver fluoride with the trans-3-bromo-2-chloro derivative afforded the trans-2-chloro-3-fluoro adduct predominantly, whereas the same reagent with the trans-2-bromo-3-chloro isomer gave nearly exclusively the cis-3-chloro-2-fluoro compound.Some mechanisms to rationalise these results are proposed.
