Unexpected products via singlet oxygen oxygenation of functionalized 5,6-dihydro-1,4-oxathiins

Authors
Cermola, F De Lorenzo, F Giordano, F Graziano, ML Iesce, MR Palumbo, G
Citation
F. Cermola et al., Unexpected products via singlet oxygen oxygenation of functionalized 5,6-dihydro-1,4-oxathiins, ORG LETT, 2(9), 2000, pp. 1205-1207
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
9
Year of publication
2000
Pages
1205 - 1207
Database
ISI
SICI code
1523-7060(20000504)2:9<1205:UPVSOO>2.0.ZU;2-E
Abstract
Singlet oxygen oxygenation of 5,6-dihydro-1,4-oxathiins substituted at C-3 with an electron-withdrawing group leads stereoselectively to ketosulfoxide s 5 and 6, instead of the expected dicarbonyl compounds 3, A mechanism invo lving an unprecedented intramolecular rearrangement of the corresponding di oxetanes 2 is proposed.