Showing papers by "Harold W. Moore published in 1992"

Rearrangements of 4-alkynylcyclobutenones. Annelated spiroepoxycyclohexadienones and quinones from 4-(1,5-alkadiynyl)-4-methoxy- or -hydroxycyclobutenones

Abstract: 4-(1,5-Dialkynyl)-4-methoxycyclobutenones 1 were shown to undergo a unique rearrangement to annelated spiroepoxides 6 upon thermolysis in toluene. The 4-hydroxy analogs also ring expand giving either quinones 13 or 14 as a function of the reaction solution concentration. This concentration dependence provides evidence for further mechanistic details of the general quinone synthesis stemming from 4-alkynyl-4-hydroxycyclobutenones