Z. Khan, T. Durst
Mar 1, 1987
Citations
0
Influential Citations
6
Citations
Journal
Canadian Journal of Chemistry
Abstract
The 1-hydroxy substituent in 1-hydroxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxides is readily replaced by alkoxy, alkylthio, and amino groups. These compounds serve as precursors of alkoxy, alkylthio, and amino substituted o-quinodimethanes. Cycloaddition reactions between a series of 1,4-disubstituted o-quinodimethanes bearing a phenyl group and one of the above heteroatoms, and typical dienophiles such as dimethyl fumarate and methyl crotonate were carried out. The phenyl group controlled both the regiochemistry and stereochemistry of these cycloaddition reactions, with the major products being trans-1-phenyl-2-carbomethoxytetrahydronaphthalenes. The amino substituted o-quinodimethanes were trapped only by dimethyl fumarate.