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

Research output: Contribution to journalArticle

44 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)463-466
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number4
DOIs
StatePublished - Jan 22 1996

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Dioxanes
Cyclization
Stereoselectivity
Alkenes
Ether
Hydrogen Peroxide
1,2,4-trioxane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of 1,2-dioxanes, 1,2,4-trioxanes, and 1,2,4-trioxepanes via cyclizations of unsaturated hydroperoxyacetals. / Dussault, Patrick H; Davies, Don R.

In: Tetrahedron Letters, Vol. 37, No. 4, 22.01.1996, p. 463-466.

Research output: Contribution to journalArticle

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