SYNTHESIS OF 1,2-DIOXANES, 1,2,4-TRIOXANES, AND 1,2,4-TRIOXEPANES VIACYCLIZATIONS OF UNSATURATED HYDROPEROXYACETALS

Authors
DUSSAULT PH DAVIES DR
Citation
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
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
4
Year of publication
1996
Pages
463 - 466
Database
ISI
SICI code
0040-4039(1996)37:4<463:SO11A1>2.0.ZU;2-#
Abstract
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.