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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

47

Issue

1

First Page

262

Last Page

263

Copyright

© Copyright 1940 by the Iowa Academy of Science, Inc.

Language

EN

File Format

application/pdf

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