The organic compounds of the stationary phase described above are orientated like bristles o n the surface of the inorganic compounds 51. Consequently the speed of the mass transfer is considerably higher here than in liquid stationary agents [sl, or ketenesW We have now prepared alkyl-o r aryl-substituted a-chloro enamines by controlled dehydrochlorination of the readily available a-chloro iminium chlo-ridesC71 ( 3 ) . phases. Further gas chromatographic experiments with columns packed with such "brushes" have shown, that the height equivalent to a theoretical plate (h) is independent of: (i) the nature of the sample (paraffins, aromatics, ether, esters, chlorinated hydrocarbons have been injected); (ii) the tem-CH 3 CH3
] [I] a-Chlorenamine (I) ohne stabilisierende elektronegative p- Die physikalischen und spektroskopischen Eigenschaften der a-Chlorenamine schlielen einen grSBeren Anteil der polaren Form im Gleichgewicht aus. Sie reagieren jedoch erwartungsgemil sowohl als Nucleophile als auch als Elektrophile entsprechend den folgenden Beispielen:
Das bicyclische Keton (I) reagiert mit Dichlormethyllithium bei ‐110°C in Trapp‐Mischung zu einem 1:1‐Gemisch der stereoisomeren Alkohole (IIa), die mit Phosphorpentachlorid bei 180°C ein Gemisch der Chloride (IIb) und (III) ergeben.
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