Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and air: regioselectivity and formation of a spirotricyclic hemiketal endoperoxidelactone

Authors
Schobert, R Siegfried, S Weingartner, J Nieuwenhuyzen, M
Citation
R. Schobert et al., Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and air: regioselectivity and formation of a spirotricyclic hemiketal endoperoxidelactone, J CHEM S P1, (17), 2001, pp. 2009-2011
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
17
Year of publication
2001
Pages
2009 - 2011
Database
ISI
SICI code
1472-7781(20010907):17<2009:OO3AWD>2.0.ZU;2-R
Abstract
The endocyclic C=C bond of 3-allyltetronic acid 1 can be selectively oxidis ed with dimethyldioxirane to give 3-allyl-3-hydroxydihydrofuran-2,4-dione 2 while 3-exo-alkylidenedihydrofuran-2,4-diones 9 are rapidly autooxidised t o furnish the spirotricyclic hemiketal endoperoxide lactones 10.