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Selenourea : ウィキペディア英語版
Selenourea

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Selenourea is the organoselenium compound with the formula SeC(NH2)2. It is a white solid. This compound features a rare example of a stable, unhindered carbon-selenium double bond. The compound is used in the synthesis of selenium heterocycles. Compared to urea, the oxo-analog of selenourea, few studies have been done on the compound due to the instability and toxicity of selenium compounds.〔Koketsu, M. Ishihara, H. “Thiourea and Selenourea and Their Applications”. ''Curr. Org. Syn.'' 2006, ''3'', pp 439-455. 〕
==Synthesis==
The compound was first synthesized in 1884 by Auguste Verneuil by the reaction of hydrogen selenide and cyanamide:〔Hope, H. “Synthesis of Selenourea”. ''Acta Chem. Scand.'', 1964, ''18'', 1800. 〕
:H2Se + NCNH2 → SeC(NH2)2
While this reaction has even found use in industrial synthesis of selenourea,〔Suvorov, V. et al. “Production of selenourea of high purity”. ''Vysokochistye Veshchestva'', 1996, ''3'', pp 17-23. 〕 more modern methods concern themselves with synthesis of substituted selenoureas. These can be synthesized using organic isoselenocyanates and secondary amines:
:RN=C=Se + NHR’R’’ → Se=C(NRH)(NR’R’’H)
Alternatively, a substituted carbodiimide could be used as follows:〔
:RN=C=NR’File:Reagents.gif Se=C(NRH)(NR’H)

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