[14839-39-5] · C24H60NiO12P4 · Tetrakis(triethyl phosphite)nickel(0) · (MW 723.41)
Physical Data: mp 108 °C; white crystals.
Solubility: sol THF, toluene.
Preparative Methods: easily synthesized by the reaction of Triethyl Phosphite, Nickel(II) Chloride, and Et2NH.5
Handling, Storage, and Precautions: is a cancer suspect agent; air sensitive; reacts with halogenated solvents; should be handled using Schlenk or glovebox techniques.
Alkylation of allylic carbonates by 1,3-dicarbonyl compounds under neutral conditions is catalyzed by [(EtO)3P]4Ni (eq 1).1 Alkenyl allyl carbonates undergo an intramolecular decarbonylative allylation with [(EtO)3P]4Ni (eq 2).6
The cycloaddition of trimethylenemethane intermediates to imines is catalyzed by [(EtO)3P]4Ni to form 4-methylenepyrrolidines (eq 3).2
[(EtO)3P]4Ni catalyzes the isomerization of 1-pentene to a mixture of cis- and trans-2-pentene (eq 4).3 At 35 °C, an equilibrium mixture (3:1:1) of trans-2-pentene, cis-2-pentene, and 1-pentene is formed.
The reaction of aldehydes with b-keto allyl esters is catalyzed by [(EtO)3P]4Ni to form b-hydroxy ketones (eq 5).4
Gregory T. Whiteker
Union Carbide Corporation, South Charleston, WV, USA