SYNTHESIS OF 1,2,4-TRIOXANES AND 1,2,4-TRIOXEPANES BY N-HALOGENOSUCCINIMIDE-MEDIATED CYCLIZATIONS OF UNSATURATED HYDROPEROXYACETALS

Authors
USHIGOE Y KANO Y NOJIMA M
Citation
Y. Ushigoe et al., SYNTHESIS OF 1,2,4-TRIOXANES AND 1,2,4-TRIOXEPANES BY N-HALOGENOSUCCINIMIDE-MEDIATED CYCLIZATIONS OF UNSATURATED HYDROPEROXYACETALS, Journal of the Chemical Society. Perkin transactions. I, (1), 1997, pp. 5-10
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
1
Year of publication
1997
Pages
5 - 10
Database
ISI
SICI code
0300-922X(1997):1<5:SO1A1B>2.0.ZU;2-I
Abstract
Ozonolyses of vinyl ethers 1a-c in CH2Cl2 in the presence of allylic a nd homoallylic alcohols 3a-c give in each case the corresponding unsat urated hydroperoxy acetals 4a-h, derived from capture of the carbonyl oxides 2a-c by the unsaturated alcohols, N-Halogenosuccinimide-mediate d cyclisations of the hydroperoxides give the corresponding 1,2,4-trio xanes and/or 1,2,4-trioxepanes, depending on the structure of the hydr operoxides and the identity of the N-halogenosuccinimides.