6-HYDROXYMETHYL-1,2,4-TRIOXANES AND DERIVATIVES - AN ALTERNATIVE 1,2,4-TRIOXANE SYNTHESIS FORM BETA-GAMMA-UNSATURATED BETA-HYDROXYHYDROPEROXIDES

Authors
BLOODWORTH AJ JOHNSON KA
Citation
Aj. Bloodworth et Ka. Johnson, 6-HYDROXYMETHYL-1,2,4-TRIOXANES AND DERIVATIVES - AN ALTERNATIVE 1,2,4-TRIOXANE SYNTHESIS FORM BETA-GAMMA-UNSATURATED BETA-HYDROXYHYDROPEROXIDES, Tetrahedron letters, 35(43), 1994, pp. 8057-8060
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
43
Year of publication
1994
Pages
8057 - 8060
Database
ISI
SICI code
0040-4039(1994)35:43<8057:6AD-AA>2.0.ZU;2-6
Abstract
Allylic hydroperoxides CH2:C(Ph)CH(OOH)CH(2)OX (X = H, CONHPh, Ac), fr om regiospecific photo-oxygenation of allylic alcohols CH3C(Ph):CHCH(2 )OX, form hemiperoxyacetals with aldehydes or ketones which upon cycli sation with mercury(II) trifluoroacetate then reduction with sodium bo rohydride diastereoselectively afford 1,2,4-trioxanes with XOCH(2) sub stituents at C-6.