356771-88-5Relevant academic research and scientific papers
Acyl Carbamoyl Selenides and Related Sulfur Isologues: Synthesis and X-Ray Structural Analyses
Kageyama, Hideki,Tani, Kazuyasu,Kato, Shinzi,Kanda, Takahiro
, p. 250 - 258 (2001)
Selenocarboxylic acids [RC(=O)SeH] were found to readily react with aryl, acyl, and arenesulfonyl isocyanates to give the corresponding acyl carbamoyl selenides 3 [RC(=O)SeC(=O)NHR', R'= aryl, C6H5CO, and 4-MeC6H4SO2] in good yields. Their tautomers [RC(=O)SeC(=NR')OH] were also detected by 1H, 13C, and 77Se NMR spectroscopies. The structure of 3 [R = 2,6-(MeO)2C6H3, R' = 4-MeC6H4] was characterized by X-ray crystallography, which showed that this molecule is stabilized by an intramolecular hydrogen bond between the carbonyl oxygen and the NH hydrogen to form a planar six-membered ring and by nonbonded interaction of ortho methoxy oxygen with the carbonyl oxygen or the selenium atoms. 4-Methoxybenzoyl and 4-methoxythiobenzoyl N-(4-methylphenyl)carbamoyl sulfides (4 and 5) were shown by X-ray crystallography to similarly have a planar intramolecular six-membered ring formed by a hydrogen bond between the carbonyl oxygen or thiocarbonyl sulfur and NH hydrogen atoms. The tautomers [RC(=E)SC(=NR')OH; E = O or S] of 4 and 5 also were detected spectroscopically. The recations of 3h (R = 4-MeOC6H4, R' = Ph) with sodium methoxide and p-toluidine gave sodium selenocarboxylate and the corresponding amides and urea as main products, respectively.
