272437-18-0Relevant articles and documents
Unexpected products via singlet oxygen oxygenation of functionalized 5,6-dihydro-1,4-oxathiins
Cermola, Flavio,De Lorenzo, Fulvio,Giordano, Federico,Graziano, M. Liliana,Iesce, M. Rosaria,Palumbo, Giovanni
, p. 1205 - 1207 (2000)
(formula presented) Singlet oxygen oxygenation of 5,6-dihydro-1,4-oxathiins substituted at C-3 with an electron-withdrawing group leads stereoselectively to ketosulfoxides 5 and 6, instead of the expected dicarbonyl compounds 3. A mechanism involving an unprecedented intramolecular rearrangement of the corresponding dioxetanes 2 is proposed.
Substituent and solvent effects on the photosensitized oxygenation of 5,6-dihydro-1,4-oxathiins. Intramolecular oxygen transfer vs normal cleavage of the dioxetane intermediates
Cermola,Iesce
, p. 4937 - 4944 (2007/10/03)
The reaction of singlet oxygen with variously substituted oxathiins 1 affords dicarbonyl compounds 4 and/or ketosulfoxides 7 and 8 depending on the nature of the substituent at C3 and on the reaction conditions. The normal fragmentation of dioxetanes 2 to
