AROMATIC SUBSTITUTION. PART V. THE MECHANISM OF THE REACTION OF PHENYLLITHIUM WITH PYRIDINES. DEUTERIUM ISOTOPE EFFECT STUDIES
Journal Article
·
· Canadian Journal of Chemistry (Canada)
The ratios of isomers formed in the reaction of 3alkylpyridines with phenyllithium under various conditions appeared to be invariant within the limits of experimental error. A number of experiments, including the reaction of phenyllithium with 3-picoline-2d and with an excess of a mixture of pyridine and pyridine-2d, are described, which establish that the hydride ion elimination stage in these nucleophilic aromatic substitutions is not important in determining the observed orientation and that the addition stage is either virtually irreversible or that the equilibrium lies far on the product side and is not rapidly reversible. A convenient procedure is described for working up the reaction mixtures. (auth)
- Research Organization:
- Univ. of Saskatchewan, Saskatoon
- Sponsoring Organization:
- USDOE
- NSA Number:
- NSA-18-005357
- OSTI ID:
- 4157848
- Journal Information:
- Canadian Journal of Chemistry (Canada), Journal Name: Canadian Journal of Chemistry (Canada) Vol. Vol: 41; ISSN CJCHA
- Country of Publication:
- Country unknown/Code not available
- Language:
- English
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