87361-13-5Relevant academic research and scientific papers
Differentially Substituted Phosphines via Decarbonylation of Acylphosphines
Yu, Rongrong,Chen, Xingyu,Martin, Stephen F.,Wang, Zhiqian
, p. 1808 - 1811 (2017/04/11)
A new route to phosphines was developed by a method that features a "pre-join and transform" process that proceeds via acylphosphine intermediates that may be readily prepared from carboxylic acids and disubstituted phosphines. The efficient decarbonylations of these acylphosphines using a nickel catalyst delivered the corresponding phosphines. This method shows that the carboxyl group can play a role similar to halides or triflates for introducing a substituted phosphorus atom on an aromatic ring.
Investigations about the Electronic Influences on the Reactivity of Aroyl- and Acyldiphenylphosphanes and their Resulting Products
Lindner, Ekkehard,Huebner, Dieter
, p. 2574 - 2590 (2007/10/02)
The air sensitive aroyl- and acyldiphenylphosphanes RC(O)-PPh2 (2a - i) are obtained by reaction of the acyl chlorides RC(O)Cl (1a - i) with (CH3)3Si-PPh2 in petroleum ether.On access of water 2a - i are hydrolysed immediately.Starting from η5-C5H5Mn(CO)2THF (3x), BrMn(CO)5 (3y) and 2c - f the stable complexes LnMn-PPh2-C(O)R (4cx,dx,ey,fx) are formed. 1b - d, f - i can be transformed into the phosphane oxides RC(O)-P(O)Ph2 (5b - d, f - i) by Arbusov reaction with Ph2POCH3.From the oxides 5b - d, f and water, by a one pot reaction of 2b - d, f with HP(O)Ph2 andoxygen, or by the action of HP(O)Ph2 on 5a, f, the phosphinates -CHR (6a - d, f) are formed. 6a is produced also in form of the picolinium chloride 6a'.The electronic influences of the different aroyl residues on the reactivity of the aroylphosphanes 2c, d, f are investigated on the basis of the electronic and i.r. spectra of 4cx, dx, fx.The unusual stability of the methoxy compound 5f can be traced back to the strong +M effect of the 4-methoxybenzoyl residue.
