THE ELECTROCHEMICAL FLUORINATION OF DERIVATIVES OF MORPHOLINE, PIPERIDINE AND CARBAZOLE

Electrochemical fluorination (ECF) of var-ious heterocyclic compounds has been investigated. In the case of 1-morpholinocyclohexene, a survey of the products of ECF is given. ECF of alpha,omega-dimorpholino- and dipiperdino-alkanes of different chain length (n = 1-6) gave the perfluoro derivatives in yields up to 45%. The crystal and molecular structure of F-dimorpholinobutane is presented. 1,3-Bis(3-methylpiperidino)propane and 1,3-bis(4-methylpiperidino)propane were fluorinated. Perhydro-N-carbazoles were fluorinated by ECF as representatives of a new class of compounds. Electrochemical fluorination of 18-crown-6 was tried without success. The mechanism of ECF for these compounds is discussed on the basis of a steric model.