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2005
Organo-phosphorus compounds
S 0080
Synthesis of 1,3,5,2λ5-Triazaphosphinines by Intramolecular Cyclization of
(N-Cyanophosphorimidoyl)guanidines and Diguanidinophosphonium Chlorides.
14- 182 — Sodium phosphonium diylide (III), the first example of a stabilized phosphonium
diylide, is synthesized as precursor for new types of phosphorylated guanidines (V) and
(X). The latter compounds are prepared by treatment of the diylide with either a stoichiometric amount of primary and secondary ammonium salts or with a sixfold excess
of these salts. By melting of both types of resulting guanidines, cyclized title compounds are obtained. The reaction of (III) with slightly less acidic chloride (VII) shows
a different behavior than with chlorides (IV). No guanidine compound is formed and
instead compound (VIII) is isolated, which rearranges to triazaphosphinine (IX) by
heating of the neat substance. — (INGUIMBERT, N.; JAEGER, L.; TAILLEFER*,
M.; BIEDERMANN, M.; CRISTAU, H.-J.; Eur. J. Org. Chem. 2004, 23, 4870-4876;
Lab. Chim. Org., CNRS, Ec. Natl. Super. Chim., F-34296 Montpellier, Fr.; Eng.) —
Klein
2005
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