35458-22-1Relevant academic research and scientific papers
Sc(OTf)3-catalyzed transfer diazenylation of 1,3-dicarbonyls with triazenes via N-N bond cleavage
Liu, Cong,Lv, Jian,Luo, Sanzhong,Cheng, Jin-Pei
supporting information, p. 5458 - 5461 (2015/01/16)
A new and efficient method for diazenylation reactions was developed with a Sc(OTf)3-catalyzed nitrogen-nitrogen bond cleavage process with triazenes. The transfer diazenylation reactions accommodate a diverse range of active methylene substrat
X-ray investigations of sulfur-containing fungicides. II. Intramolecular forces governing the conformation of four novel α-phenylazo- and α-phenylhydrazono-β-ketosulfones
Wolf
, p. 54 - 62 (2007/10/03)
The crystal and molecular structures of four novel β-ketosulfones, phenyl benzoyl(phenylhydrazono)methyl sulfone (I), phenyl benzoyl(4-nitrophenylhydrazono)methyl sulfone (II), (benzoyl)(phenyl)(phenylazo)methyl phenyl sulfone (III) and (benzoyl)(phenyl)(3-chlorophenylazo)-methyl 4-tolyl sulfone (IV), have been investigated using X-ray analysis and density functional theory supplemented by ab initio Hartree-Fock calculations. The conformations of (I) and (II) are stabilized by strong intramolecular resonance-assisted hydrogen bonds formed between the sulfonyl and the α-hydrazono moieties. The following increase of a positive charge on the S atoms is compensated via π-conjugation and stereoelectronic back-donation from the nearby β-carbonyl group. Compounds (III) and (IV) adopt a strongly distorted propeller shape with pivotal tetrahedral Cl atoms. Distortion mostly follows from the approximate coplanarity of the α-azophenyl and α-phenyl moieties opposite each other. The main stereoelectronic interactions involve the donation of electron density from the α-azo N2 towards the sulfonyl S and the β-carbonyl C2 atoms.
