ISSN:
0009-2940
Keywords:
Phosphane
;
2-pyridyl-
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis and Reactions of 2-Pyridylphosphane, 2—C5NH4-PH2By reduction of diethyl 2-pyridylphosphonate (1) with LiAlH4 2-pyridylphosphane (2) is accessible in ≍80% yield. H/D exchange experiments and acid/base exchange reactions between 2 and PhPHLi or Ph2PLi show (2) to be a stronger pH acid than PhPH2 and Ph2PH. Silylation of the lithium phosphides 2-C5NH4-PRLi (R — H, SiMe3) with Me3SiCl affords the corresponding silyl derivatives 2-C5NH4-PR2 with CH3I or CH2Cl2 yields the mono- or bidentate secondary phosphanes 2-C5NH4-PHMe (6) and 2-C5NH4PHCH2PH-2-C5H4N (5), respectively. On treatment of 2 with CH3I or HCl the pyridinium salts [(2-C5NH4R)PH2]+X- (R — H, Me; X= Cl, I) are formed. However, coordination of 2 to transition metals in low oxidation states occurs by the phosphorus atom. Addition of the PH bonds in 2 to the activated C—C double bonds in acrylic acid esters, mesityl oxide, cinnamnic acid esters, and dimethyl vinylphosphonate leads to chiral P,N hybrid ligands with functional groups in the alkyl side chain.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230510
