Issue 1, 1970

Aromatic substitution. Part XXV. Reaction of 3-picoline with some substituted phenyl-lithium derivatives

Abstract

A study of the reactions of o-tolyl-, o-ethylphenyl-, and p-methoxyphenyl-lithium with 3-picoline has shown that the substituent has little effect upon the ratio of the 2,3- and 2,5-isomers formed. o-Tolyl-lithium gave, in addition, some 3-methyl-5-o-tolylpyridine, and 3-methyl-1,2,5,6-tetrahydro-2-o-tolylpyridine could be isolated under certain conditions. The latter arises by disproportionation of the intermediate σ-complex while the former probably results from the attack of this σ-complex by o-tolyl-lithium. An attempt to reduce 3-methyl-2-o-tolylpyridine to the tetrahydro-derivative with lithium aluminium hydride and aluminium chloride was unsuccessful.

Article information

Article type
Paper

J. Chem. Soc. C, 1970, 128-131

Aromatic substitution. Part XXV. Reaction of 3-picoline with some substituted phenyl-lithium derivatives

R. A. Abramovitch, C. S. Giam and G. A. Poulton, J. Chem. Soc. C, 1970, 128 DOI: 10.1039/J39700000128

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements