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. 2000 May 4;2(9):1205-7.
doi: 10.1021/ol000023i.

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

F Cermola  1 , De Lorenzo F, F Giordano, ML Graziano, MR Iesce, G Palumbo
Affiliations

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

F Cermola et al. Org Lett. .

Abstract

[formula: see text] Single 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.

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