Organic selenocyanates

Organic selenocyanates are organoselenium compounds with the general formula RSeCN. They are generally colorless, air-stable solids or liquids with repulsive odors. In terms of structure, synthesis, and reactivity, selenocyanates and thiocyanates behave similarly.

Preparation

Alkyl selenocyanates are generally prepared by treatment of potassium selenocyanate with alkyl halides in alcohol or acetone solution. Aryl selenocyanates are generally prepared by treatment of potassium selenocyanate with aryl diazonium salts.^[1]

Reactions

Organic selenocyanates can be reduced to the selenol, which readily oxidize to the diselenide:

RSeCN + 2 e⁻ → RSe⁻ + CN⁻

RSe⁻ + H⁺ → RSeH

2 RSeH + 0.5 O₂ → RSeSeR + H₂O

Oxidation of selenocyanates gives the seleninic acids.^[1]

References

^ ^a ^b E. Bulka (1977). "Selenocyanates and Related Compounds". In Saul Patai (ed.). Cyanates and Their Thio Derivatives: Part 2, Volume 2. PATAI'S Chemistry of Functional Groups. pp. 619–818. doi:10.1002/9780470771532.ch3. ISBN 9780470771532.

[Patai-1] E. Bulka (1977). "Selenocyanates and Related Compounds". In Saul Patai (ed.). Cyanates and Their Thio Derivatives: Part 2, Volume 2. PATAI'S Chemistry of Functional Groups. pp. 619–818. doi:10.1002/9780470771532.ch3. ISBN 9780470771532.

[1]