Ph. Dussault et Dr. Davies, SYNTHESIS OF 1,2-DIOXANES, 1,2,4-TRIOXANES, AND 1,2,4-TRIOXEPANES VIACYCLIZATIONS OF UNSATURATED HYDROPEROXYACETALS, Tetrahedron letters, 37(4), 1996, pp. 463-466
Unsaturated hydroperoxyacetals and -ketals undergo electrophilic cycli
zation to afford dioxanes, trioxanes or trioxepanes. Stereoselectivity
is low for trioxepanes, moderate for dioxanes, and high for trioxanes
. The hydroperoxide starting materials are readily prepared through se
lective ozonolysis of an enol ether in the presence of an internal or
external alkene.