Azomethine derivatives. Part IX. Preparation of dialkylideneammonium salts via diarylketiminodiphenylmethyl chlorides
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in J. Chem. Soc. A
- p. 1742-1745
- https://doi.org/10.1039/j19690001742
Abstract
The diarylketiminodiphenylmethyl chlorides Ph2C:NCClPh2 and p-tolyl2C:NCClPh2 have been prepared from Ph2CCl2 and R2C:NLi in benzene. Reactions, normally in toluene, between these chlorides and the Lewis acids BCl3, AlCl3, and SbCl5 have been used to prepare the dialkylideneammonium salts Ph2C:N:CPh2 + MXn –(MXn –= BCl4 –, AlCl4 –, or SbCl6 –) and p-tolyl2C:N:CPh2 + SbCl6 –, the ionic structures of which are supported by their electrical conductivities in nitrobenzene, and also by a band in their i.r. spectra centred at 1845 cm.–1, assigned to ν(C:N:C). The ion Ph2C:N:CPh2 + also features prominently in the mass spectrum of Ph2C:NCClPh2. Unsuccessful attempts to prepare the tetraphenylborate Ph2C:N:CPh2 + BPh4 – from Ph2C:NCClPh2+ NaBPh4, and from Ph2C:NH2 +Cl–+ NaBPh4+ Ph2C:Y (Y = O or NH) are described. Ph2C:NH2 + Cl– and NaBPh4 in boiling toluene gave Ph2C:NBPh2. Ph2CCl2 and 2Ph2C:NLi in boiling toluene gave (Ph2C:N)2CPh2.Keywords
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