101730

4-Phenyl-1,2,3-thiadiazole

4-Phenyl-1,2,3-thiadiazole 1 is a crystalline solid ( mp 78°C). It is thermally stable up to >150°C but decomposes at 220°C, or by FVP at 500 °C to form the unstable phenylthioketene (1). 1 is a convenient source of the 2-phenylethynethiolate anion 2, which can be generated by the action of bases such as potassium hydroxide and potassium t-butoxide (2). The alkynethiolates are reactive species which can react either with electrophiles or nucleophiles affording a number of sulfur-containing products including thiocarbonyl compounds, alkynesulfides and 1,3-dithioles (3) (See Scheme).

 

References

(1)	G. Seybold, C. Heibl Angew. Chem. 1975, 87, 171
	H. Meier , H. Bühl J. Het. Chem. 1975, 12, 605
(2)	R. Raap, R. G. Michetich Can. J. Chem. 1968, 46, 1057
(3)	See G. Labbé, B. Dhooge, W. Dehaen Molecules 1996, 1, 190 and references cited therein