111709-02-5Relevant articles and documents
Erratum to New Heterocyclic Precursors for Thermal Generation of Reactive, Electron-Rich 1,2-Diaza-1,3-butadienes
Boeckman, Robert K.,Ge, Ping,Reed, Jessica E.
, p. 1635 - 1636 (2002)
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Regioselectivity in the Photochemical Ring Contraction of 4-Diazopyrazolidine-3,5-diones to give Aza-β-lactams
Lawton, Geoffrey,Moody, Christopher J.,Pearson, Christopher J.,Williams, David J.
, p. 885 - 898 (2007/10/02)
Irradiation of 4-diazopyrazolidine-3,5-diones (15) in the presence of alcohols or water gave mixtures of the isomeric 1,2-diazetidinones (16) and (17), formed by competing photochemical Wolff rearrangement of the two nitrogen groups, followed by reaction of the resulting ketenes with the nucleophile.Some regioselectivity is observed in the ring contraction process, and the relative order of migration of nitrogen groups is NPh>NCHPh2NCH2PhNMe>NCH2CO2Et.The structures of the 1,2-diazetidinones (17c) and (24) were confirmed by X-ray crystallography, and a crystal structure of the diazo compound (15g) was also obtained.Possible reasons for the regioselectivity in the ring contraction are discussed.