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Photochemical stabilization of aryldiazonium salts by crown ether complexation

✍ Scribed by Richard A. Bartsch; Neil F. Haddock; Douglas W. McCann

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 194 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)83352-9

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✦ Synopsis

Crown ether complexes of aryldiazonium ions exhibit markedly enhanced thermal stability relative to the corresponding uncomplexed salts. ' Thus, the thermal decomposition (Schiemann reaction) of P-tert-butylbenzenediazonium fluoroborate in 1,2-dichloroethane is retarded by the presence of 18-crown-6, dicyclohexyl-18-crown-6, and dibenzo-18-crown-6. Kinetic studies demonstrate that the uncomplexed diazonium fluoroborate decomposes at least one hundred times faster than the crown ether-complexed salt.

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