Synthesis of 1,3,5,2λ⁵‐Triazaphosphinines by Intramolecular Cyclisation of (N‐Cyanophosphorimidoyl)guanidines and Diguanidinophosphonium Chlorides

Abstract

The sodium phosphonium diylide Na[Ph 2 P(NCN) 2 ] (3) − the first example of a stabilised phosphonium diylide − was synthesised by treatment of sodium diphenylphosphide with 2 equiv. of cyanic azide. Compound 3 reacted with alkyl-and arylammonium salts [RRЈNH 2 ]Cl {R = PhCH 2 , tBu, Ph; RЈ = H; RRЈ = −[(CH 2 ) 2 O(CH 2 ) 2 ]−}. Depending on the molar ratios (1:1 or 1:2), (N-cyano-P,P-diphenylphosphorimidoyl)guanidines Ph 2 P(NCN)N=C(NH 2 )NRRЈ (8)

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C–P Bonds by Sodium

“…In the literature, the reactions of Ph 2 PCl with metallic sodium generating Ph 2 PNa were carried out in refluxing THF for a long time. , In contrast, as shown in Table , when SD (3 mmol) was added to a THF (2 mL) solution of Ph 2 PCl (90 μL, 1 mmol) at room temperature , the reaction took place rapidly, and Ph 2 PNa was generated nearly quantitatively by 0.5 h (run 1) . The reaction is clean, and no other phosphorus species could be detected at all from the reaction mixture.…”

A Convenient Synthesis of Novel 6-Aryl-5-phenyl-5-oxido-6,7-dihydro[1,3,4,2]thiadiazaphospholo[5,4-c][1,2,4,5]triazaphosphinines

“…7 The triazaphosphinine class has possible six isomers as shown in Figure 1. To our best knowledge, the isomers of 1,2,3,4-triazaphosphinine (I), 8-10 1,2,4,3-triazaphosphinine (IV) 11,12 and 1,3,5,2-triazaphosphinine (VI) [13][14][15][16][17][18][19][20][21] have been reported. Previously, we constructed some isomers of 1,2,4,5-triazaphosphinine (III) fused with pyridine, pyrimidine and 1,2,4-triazine moieties.…”