Phosphorus–nitrogen compounds. Part XX. The reaction of piperidine with hexachlorocyclotriphosphazatriene; the replacement pattern and the structure of the products; the “cis-effect”
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in J. Chem. Soc. A
- p. 908-913
- https://doi.org/10.1039/j19660000908
Abstract
The reaction of hexachlorocyclotriphosphazatriene with piperidine leads to a series of derivatives, N3P3Cl6–n(NC5H10)n(n= 1, 2, 3, 4, or 6). Pairs of isomers were obtained for the di-(cis and trans) and tri-(trans and geminal) derivatives; a third tri-isomer (cis) was obtained by an isomerisation reaction. The preparation of mixed dimethylamino-piperidino-derivatives, N3P3(NMe2)6–n(NC5H10)n, by reaction of chlorodimethylaminocyclotriphosphazatrienes, N3P3Cl6–n(NMe2)n, and of the above chloro-piperidino-derivatives with piperidine and dimethylamine, respectively, leads to structural assignments for the chloro-piperidino-derivatives. These assignments indicate that the replacement by piperidino residues in hexachlorocyclotriphosphazatriene proceeds mainly by a non-geminal reaction scheme. A “cis-effect” is postulated to account for the observed reaction pattern of dimethylamine and piperidine with hexachlorocyclotriphosphazatriene. The 1H n.m.r. spectra of all the above derivatives are reported and discussed.Keywords
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