104703-77-7Relevant academic research and scientific papers
E,E- and E,Z-α-phenyl-α'-acetoxyorthoquinodimethane: steric and electronic control of cycloaddition reactions
Charlton, James L.,Alauddin, Mian M.,Penner, Glenn H.
, p. 793 - 798 (2007/10/02)
E,E- and E,Z-α-phenyl-α'-acetoxyorthoquinodimethanes have been prepared from the corresponding cis- and trans-1-acetoxy-3-phenyl-1,3-dihydrobenzothiophene-2,2-dioxides.The regio- and diastereoselectivity of the addition reactions with dimethyl fumarate, dimethyl maleate, maleic anhydride, and methyl crotonate have been determined.Ab initio calculations have been carried out on orthoquinodimethane and its α-phenyl and α-oxy derivatives.A correlation has been made between the steric and electronic properties of the orthoquinodimethanes and the regio- and diastereoselectivity of their Diels-Alder reactions.
