isoselenocyanate

Isoselenocyanate is an organoselenium compound that contains the isoselenocyanate functional group RN=C=Se, where R is an organic substituent. It is the selenium analogue of the isocyanate group RN=C=O and is related to isothiocyanates RN=C=S. These compounds are studied within the broader field of chalcogen-nitrogen chemistry and are encountered mainly in academic research rather than in commercial products.

In isoselenocyanates, the central carbon is doubly bonded to nitrogen and selenium, giving a linear N=C=Se core. The nitrogen bears the organic substituent R, and the overall geometry around the N–C–Se linkage is typically linear at the carbon, with substantial multiple-bond character.

Isoselenocyanates are prepared in limited, research contexts. Common approaches include dehydration or rearrangement of N-selenocarbamates, or conversion of selenoureas or related precursors under dehydrating conditions to form the RN=C=Se motif. Because these compounds are not widely produced, synthetic routes vary by laboratory and target R groups.

The RN=C=Se group is reactive toward nucleophiles at the carbon center, enabling functionalization to give substituted selenocyanates or related products. Isoselenocyanates are primarily of interest as building blocks in organic and organoselenium chemistry and as tools for studying the chemistry of cumulative heteroatom systems. They are investigated in small-scale laboratory studies rather than as bulk reagents.

Like other selenium-containing compounds, isoselenocyanates can be toxic and irritating to the skin and eyes and may pose environmental hazards. Proper handling includes use of protective equipment, work in a well-ventilated area, and appropriate waste disposal.