E,E- and E,Z-α-phenyl-α′-acetoxyorthoquinodimethane: steric and electronic control of cycloaddition reactions
- 1 April 1986
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 64 (4) , 793-798
- https://doi.org/10.1139/v86-130
Abstract
E,E- and E,Z-α-phenyl-α′-acetoxyorthoquinodimethanes have been prepared from the corresponding cis- and trans-1-acetoxy-3-phenyl-1,3-dihydrobenzo[c]thiophene-2,2-dioxides. The regio- and diastereoselectivity of the addition reactions with dimethyl fumarate, dimethyl maleate, maleic anhydride, and methyl crotonate have been determined. Abinitio 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.This publication has 2 references indexed in Scilit:
- Stereoselective synthesis of an analog of podophyllotoxin by an intramolecular Diels-Alder reactionThe Journal of Organic Chemistry, 1985
- The synthesis of lignans and related structures using quinodimethanes and isobenzofurans: approaches to the podophyllinsJournal of the Chemical Society, Perkin Transactions 1, 1984