Synthesis of 1,2-dioxanes, 1,2,4-trioxanes, and 1,2,4-trioxepanes via cyclizations of unsaturated hydroperoxyacetals

Patrick H. Dussault; Don R. Davies

doi:10.1016/0040-4039(95)02199-X

Synthesis of 1,2-dioxanes, 1,2,4-trioxanes, and 1,2,4-trioxepanes via cyclizations of unsaturated hydroperoxyacetals

Patrick H. Dussault, Don R. Davies

Chemistry

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52 Scopus citations

Abstract

Unsaturated hydroperoxyacetals and -ketals undergo electrophilic cyclization 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 selective ozonolysis of an enol ether in the presence of an internal or external alkene.

Original language	English (US)
Pages (from-to)	463-466
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	4
DOIs	https://doi.org/10.1016/0040-4039(95)02199-X
State	Published - Jan 22 1996

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Unsaturated hydroperoxyacetals and -ketals undergo electrophilic cyclization 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 selective ozonolysis of an enol ether in the presence of an internal or external alkene.",

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AU - Davies, Don R.

PY - 1996/1/22

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N2 - Unsaturated hydroperoxyacetals and -ketals undergo electrophilic cyclization 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 selective ozonolysis of an enol ether in the presence of an internal or external alkene.

AB - Unsaturated hydroperoxyacetals and -ketals undergo electrophilic cyclization 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 selective ozonolysis of an enol ether in the presence of an internal or external alkene.

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Synthesis of 1,2-dioxanes, 1,2,4-trioxanes, and 1,2,4-trioxepanes via cyclizations of unsaturated hydroperoxyacetals

Abstract

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