Document Type

Research

Abstract

The halogen-metal interconversion reaction now makes possible the preparation of hitherto difficultly or completely inaccessible organolithium compounds from the corresponding bromo- or iodo-nuclear substituted nitrogen heterocycles by means of other organolithium compounds like n-propyllithium and n-butyllithium : C₅H₄NBr +n-C₄H₉Li ( 3-bromopyridine) → C₅H₄NLi +n-C₄H₉Br ( 3-pyridyllithium). These organolithium compounds of the nitrogen heterocycles are of a relatively high order of reactivity with other functional groups. Some of the types reported on in the pyridine series are: 1. 3-pyridyllithium in 70 per cent yield from 3-bromopyridine and n-butyllithium, 2. 3-quinolyllithium in 52 per cent yield from 3-bromopyridine, 3. 5-bromo-3-pyridyllithium in 41 per cent yield from 3, 5-dibromopyridine and slightly more than two equivalents of n-butyllithium. In the carbazole series, some of the organolithium compounds rep0rted are: 1. N-ethyl-2, 8-dilithiocarbazole in 84-91 per cent yield from N-ethyl-2, 8-dibromocarbazole, and in 79-92 per cent yield from the corresponding di-iodo-compound. 2. N-ethyl-2-lithiocarbazole 1 from the corresponding iodocarbazole in 68 per cent yield.

Publication Date

1940

Journal Title

Proceedings of the Iowa Academy of Science

Volume

Issue

First Page

262

Last Page

263

Copyright

Language

File Format

application/pdf

Recommended Citation

Spatz, Sydney M. and Gilman, H. (1940) "New Synthetic Tools in the Pyridine, Quinoline and Other Nitrogen-Heterocyclic Series," Proceedings of the Iowa Academy of Science, 47(1), 262-263.
Available at: https://scholarworks.uni.edu/pias/vol47/iss1/51

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New Synthetic Tools in the Pyridine, Quinoline and Other Nitrogen-Heterocyclic Series

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