34879-72-6Relevant academic research and scientific papers
α-Bromo Isocyanates
Reck, Reinhard,Jochims, Johannes C.
, p. 860 - 870 (2007/10/02)
Isocyanates R1R2CH-NCO (1a - j) react with N-bromosuccinimide photochemically to form α-bromo isocyanates R1R2CBr-NCO (2a - j) in high yields.Methyl isocyanate (1i) gives a mixture of tribromomethyl isocyanate (2i) and carbonyl bromide isocyanide dibromide (2i').Neopentyl isocyanate (1j) is brominated to the tautomeric dibromo isocyanates 2j and 2j'.The barrier to hindered rotation of the tert-butyl group in 2j amounts to δG+/-250 = 51 kJmol-1.With potassium thiocyanate the α-bromo isocyanates form the α-isothiocyanato isocyanates 5.Reactions of α-bromo isocyanates with hydrocyanic acid, amines, ureas, and alcohol s are described.Reaction with N-methylhydroxylamine yields the oxadiazolidinones 13.
