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Umsetzung von 2‐Azidoalkoholen mit Trialkylphosphiten Bildung von Aziridinen und Amidophosphorsäureesten via Imidophosphorsäureester und 1,3,2λ 5 ‐Oxazaphospholidine
Author(s) -
Willeit Armin,
Müller Ernst Peter,
Peringer Paul
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660812
Subject(s) - chemistry , yield (engineering) , medicinal chemistry , alkyl , reaction conditions , organic chemistry , catalysis , materials science , metallurgy
Reaction of 2‐Azidoalcohols with Trialkylphosphites. Formation of Aziridines and Amidophosphates via Imidophosphates and 1,3,2λ 5 ‐Oxazaphospholidines The 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‐1,3,2λ 5 ‐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 1,3,2λ 5 ‐oxazaphospholidines 16–22 are transformed to aziridines 24, 26 , and 35–38 (Scheme 5). The reactions of the imidophosphates seem to proceed via 1,3,2λ 5 ‐oxazaphospholidines.