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Reductive N Alkylation of Cyclo[8]pyrroles

✍ Scribed by Thomas Köhler; Zhongping Ou; Jeong Tae Lee; Daniel Seidel; Vincent Lynch; Karl M. Kadish; Jonathan L. Sessler

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
201 KB
Volume
44
Category
Article
ISSN
0044-8249

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✦ Synopsis

Cyclo[8]

pyrrole (1), although lacking bridging meso carbon atoms, may be considered as a larger analogue of porphyrin (2) in that it is flat and aromatic (see Scheme 1). [1] For this reason, we have been interested in exploring the chemical behavior of cyclo [8]pyrrole and contrasting it to that of the porphyrins. In previous work, we have found that cyclo[8]pyrrole in its diprotonated form may be reduced electrochemically to produce a formally antiaromatic 32-p-electron species under conditions that are much less forcing than those needed to reduce typical porphyrins. [2] Here we report that cyclo[8]pyrrole, upon treatment with NaH and an alkyl halide, undergoes chemical reduction to produce an octa-N-

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Electrochemically generated tetraethylammonium peroxy-corresponding N-alkylated pyrroles in high yields. C-Alkylated pyrroles have not been isolated in any case dicarbonate (TEAPC) and tetraethylammonium carbonate (TEAC) react under very mild conditions with pyrroles reported. affording, after addit