Geminale Vinyldiazide, IX Oxazole aus 3,3‐Diazido‐2‐cyanacrylsäure‐methylester und Aminen

Geminal Vinyl Diazides, IX. ‐ Oxazoles from Methyl 3,3‐Diazido‐2‐cyanoacrylate and Amines Reaction of methyl 3,3‐diazido‐2‐cyanoacrylate (1) with amines 2 at ‐ 25°C yields methyl 3‐azido‐2‐cyanoacrylates 3, which on thermal or photochemical treatment give azirines 7 and/or oxazoles 10 (X‐ray structure analysis of 101), respectively. On the contrary, 1 reacts at 20°C with amines 13 to form methyl 2‐(cyanimino)glycinates 14. Reaction of methyl 3‐azido‐2‐cyanoacrylates 30,1 with triphenylphosphane leads to Staudinger adducts 15, which are transformed by elimination of nitrogen into phosphane imides 16.