Synthesis of 3-hydroperoxy (or hydroxy)substituted 1,2-dioxanes and 1,2-dioxepanes by the ozonolysis of unsaturated hydroperoxy acetals

Authors
Tokuyasu, T Ito, T Masuyama, A Nojima, M
Citation
T. Tokuyasu et al., Synthesis of 3-hydroperoxy (or hydroxy)substituted 1,2-dioxanes and 1,2-dioxepanes by the ozonolysis of unsaturated hydroperoxy acetals, HETEROCYCLE, 53(6), 2000, pp. 1293-1304
Citations number
56
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
6
Year of publication
2000
Pages
1293 - 1304
Database
ISI
SICI code
0385-5414(20000601)53:6<1293:SO3(H1>2.0.ZU;2-N
Abstract
Mono-ozonolysis of dienes in methanol gave in each case the corresponding u nsaturated hydroperoxy acetals. The reaction of the hydroperoxides with ozo ne in the solvent system such as AcOH-CH2Cl2 resulted in the production of the corresponding hydroperoxy (or hydroxy)substituted 1,2-dioxanes or 1,2-d ioxepanes in good yield. By the treatment of the derived products with TMSO Tf-Et3SiH, replacement of the methoxy (or hydroxy) group by hydrogen was ac complished.