Umsetzung von 2-Azidoalkoholen mit Trialkylphosphiten. Bildung von Aziridinen und Amidophosphorsaeureestern via Imidophosphorsaeureester und 1,3,2λ5-Oxazaphospholidine

Article abstract of DOI:10.1002/hlca.19830660812

The 2-azidoalcohols 1 and 2 react with trialkyl phosphites to trialkyl (2-hydroxyalkyl)imidophosphates 10, 14, and 15 respectively, whereas the 2-azidoalcohols 3-7 yield the 2,2,2-trialkoxy-1,3,2λ⁵-oxazaphospholidines 16-22 under the same reaction conditions (Scheme 2).The dialkyl (2-hydroxyalkyl)amidophosphates 23, 25, and 27-34 are obtained by the reaction of 10, and 14-22 with water (Scheme 3 and 4).By reaction with alcohols, however, both the imidophosphates 10, 14, and 15 and the 1,3,2λ⁵-oxazaphospholidines 16-22 are transformed to aziridines 24, 26, and 35-38 (S cheme 5).The reactions of the imidophosphates seem to proceed via 1,3,2λ⁵-oxazaphospholidines.