ISSN:
1572-9001
Keywords:
Carbocation
;
tetrafluoroborate salt
;
multiannulation process
;
ketene imines
;
electrochemical oxidation
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The electrochemical generation of stable carbocations, among other heterocyclic products, by a unique electrochemical process involving the anodic oxidation of aryl-substituted ketene imines is described. The electrochemical oxidation undergoes an unusual multiannulation process to form these types of products by intermolecular cyclization. The X-ray crystal structures of two carbocation tetrafluoroborate salts,4c and4d, of which the latter is solvated by CH2Cl2, are presented. We have observed that one of the B-F bonds in4c is relatively long with respect to the other three similar in length B-F bonds, while in the solvated salt (4d·CH2Cl2), one of the B-F bonds is particularly short relative to its congeners. In both cases, the “exceptional” B-F bonds are oriented toward the positive center of the carbocation. These phenomena are compared with other known X-ray structures of organic tetrafluoroborate salts and discussed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00677369
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