- A Catalyst-Free Synthesis of Phosphinic Amides Using O-Benzoylhydroxylamines
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A practical approach for the synthesis of phosphinic amides via the coupling of secondary phosphine oxides (SPOs) with O-benzoylhydroxylamines has been reported. Simply heating the mixture of SPOs and O-benzoylhydroxylamines in the presence of K2/su
- Zhu, Rui,Pan, Chongqing,Gu, Zhenhua
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- Synthesis of nonsymmetrical dialkylamines on the basis of diphenylphosphinic amides
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A facile method for the synthesis of nonsymmetrical dialkylamines (C nH2n+1)2NH (n = 1-12) using the Ph 2P(O) protecting group was developed. The method includes successive transformation of monoalkylamines to primary diphenylphosphinic N-alkylamides Ph2P(O)NHR' (R' = CnH2n+1, n = 1-12) by the Todd-Atherton reaction, phase transfer N-alkylation of these compounds, and hydrolysis of the secondary amides Ph2P(O)NR'R″ thus formed. When the (EtO)2P(O) and Bu2P(O) protecting groups are used, N-alkylation of primary amides is accompanied by the formation of Et-O and P-N bond cleavage products, respectively. A study of the stability of the N-alkylamides R2P(O)NHR' (R = Ph, p-MeC6H4, p-CIC6H4, Bu) under strong alkaline conditions used in the phase transfer N-alkylation showed that an increase in the electron-donating ability of substituents at both the nitrogen atom and the phosphorus atom results in a decrease in the degree of P-N bond cleavage. The primary and secondary diphenylphosphinic amides containing a β-hydroxyethyl group at the nitrogen atom are extremely unstable under the alkaline conditions and are converted quantitatively to the diphenylphosphinic acid salt.
- Bondarenko,Kharlamov,Vendilo
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experimental part
p. 1872 - 1885
(2011/01/06)
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