82685-05-0Relevant academic research and scientific papers
Preparation, Structure, and Thermal Behaviour of (2-Chloroacyl)diphenylphosphanes - a New Pathway to Chloroketenes
Lindner, Ekkehard,Steinwand, Michael,Hoehne, Sigurd
, p. 2181 - 2191 (2007/10/02)
The chlorinated acylphosphanes RC(O)-PPh2 (2a - f) are obtained by the reaction of the acyl chlorides RC(O)Cl (1a - f) with (CH3)3SiPPh2 in ether at -80 deg C.HCCl2C(O)-PPh2 (2c) crystallizes monoclinicly in the space group P21/c with Z = 8.As a result of steric caused electronic effects with increasing degree of chlorination in the series 2b -> 2c -> 2d a stepwise high field shift of the signals in the 31P-NMR spectra is observed. 2b - d, f are thermally labile and decompose with formation of ClPPh2 (3) and ketene at 80 deg C.The chloroketenes HCClCO (4) and CH3CClCO (5) are detected for the first time directly by means of their 13C NMR spectra.Between 0 and 40 deg C 2d also yields Cl3PPh2 (6).With cyclohexene or aniline 4 reacts to give the trapping products 8 and 9, respectively.
