K. Yeung, N. Meanwell, Yi Li
Mar 19, 1998
Citations
0
Influential Citations
19
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 4-Hydroxymethylbenzisothiazolone-1,1-dioxide could be facilely synthesised via a highly regioselective Diels-Alder cycloaddition between furfuryl alcohol and 2-( tert -butyl)-isothiazolone-1,1-dioxide, followed by aromatization of the adduct under basic conditions. A secondary effect from intramolecular hydrogen bonding is found also to influence the regioselectivity of the cycloaddition. Unequivocal proof of the regiochemistry of the Diels-Alder reaction is provided by X-ray crystallography and ab initio calculations showed electronic and steric effects on transition structure asynchronicity.