New rac‐XP(O)(OC6H5)(NHC6H4‐p‐CH3) [X = N(CH3)(cyclo‐C6H11) and NH(C3H5)] and rac‐(C6H5CH2NH)P(O)(OC6H5)(NH‐cyclo‐C6H11) mixed‐amide phosphinates
The mixed‐amide phosphinates, rac‐phenyl (N‐methylcyclohexylamido)(p‐tolylamido)phosphinate, C20H27N2O2P, (I), and rac‐phenyl (allylamido)(p‐tolylamido)phosphinate, C16H19N2O2P, (II), were synthesized from the racemic phosphorus–chlorine compound (R,S)‐(Cl)P(O)(OC6H5)(NHC6H4‐p‐CH3). Furthermore, the phosphorus–chlorine compound ClP(O)(OC6H5)(NH‐cyclo‐C6H11) was synthesized for the first time and used for the synthesis of rac‐phenyl (benzylamido)(cyclohexylamido)phosphinate, C19H25N2O2P, (III). The strategies for the synthesis of racemic mixed‐amide phosphinates are discussed. The P atom in each compound is in a distorted tetrahedral (N1)P(=O)(O)(N2) environment. In (I) and (II), the p‐tolylamido substituent makes a longer P—N bond than those involving the N‐methylcyclohexylamido and allylamido substituents. In (III), the differences between the P—N bond lengths involving the cyclohexylamido and benzylamido substituents are not significant. In all three structures, the phosphoryl O atom takes part with the N—H unit in hydrogen‐bonding interactions, viz. an N—H...O=P hydrogen bond for (I) and (N—H)(N—H)...O=P hydrogen bonds for (II) and (III), building linear arrangements along  for (I) and along  for (III), and a ladder arrangement along  for (II).
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Document Type: Research Article
Publication date: October 15, 2013