ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reaction of 2-Azidoalcohols with Trialkylphosphites. Formation of Aziridines and Amidophosphates via Imidophosphates and 1,3,2λ5-OxazaphospholidinesThe 2-azidoalcohols 1 and 2 react with trialkyl phosphites to trialkyl (2-hydroxy-alkyl)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 (Scheme 5). The reactions of the imidophosphates seem to proceed via 1,3,2λ5-oxazaphospholidines.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19830660812
