175467-78-4Relevant articles and documents
3-Alkylidene-2-azetidinethiones: Useful intermediates for the synthesis of 3-substituted 2-azetidinethiones
Nieschalk, Jens,Spanka, Carsten,Schaumann, Ernst
, p. 135 - 140 (2007/10/03)
3-Lithiated 2-azetidinethiones 1 were allowed to react with carbonyl compounds to give 3-(1-hydroxyalkyl)-2-azetidinethiones 3, 4 which were converted into α,β-unsaturated β-thiolactams 7, 8, 10 by elimination procedures. Alternatively, the title compounds were prepared by Peterson olefination of 3-trimethylsilyl-2-azetidinethiones 9. Reactions of 7, 8, 10 with thiophenol or sodium diethyl malonate provided the Michael adducts 11. E/Z, Photoisomerization of 7, 8 by visible light was observed. On deprotonation, 7a, 8a underwent allyl rearrangement to 13. VCH Verlagsgesellschaft mbH, 1996.