Hostname: page-component-78c5997874-ndw9j Total loading time: 0 Render date: 2024-11-10T21:33:40.528Z Has data issue: false hasContentIssue false

XXI.—The Synthesis of Some Methyl- and Dimethylfluoranthenes*

Published online by Cambridge University Press:  14 February 2012

Abstract

3-Methylfluorene-9-propionic acid (1) with hydrofluoric acid undergoes ring-closure on the substituted ring to give 1,2,3,10b-tetrahydro-5-methylfluoranthen-3-one (II).

Wolff-Kishner reduction of the ketone yielded l,2,3,10b-tetrahydro-5-methylfluoranthene which on dehydrogenation gave 2-methylfluoranthene (III, R=H) identical with a sample prepared according to the method of Tucker (1952) and differing from 8-methylfluoranthene. This proved that ring-closure of (I) had occurred as expected on the methyl-bearing benzene ring. In this instance ring-closure occurs in the position meta to the methyl group and is reminiscent of the similar ring-closure of 2-phenyl-2-p-tolylpropionic acid to give 6-methyl-3-phenylindanone (Pfeiffer and Roos 1941). It thus provided a further example of the limitations of von Braun's statement that Friedel-Crafts ring-closure occurs much less readily at the position meta to a methyl group than on a phenyl ring (von Braun, Manz and Reinsch 1928).

Type
Research Article
Copyright
Copyright © Royal Society of Edinburgh 1972

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

References to Literature

Braun, J. Von, Manz, A. and Reinsch, E., 1928. Justus Liebigs Annln Chem., 468, 277.CrossRefGoogle Scholar
Campbell, N. and Andrew, H. F., 1965. Proc. Roy. Soc. Edinb., A, 66, 252.Google Scholar
Campbell, N. and Fairfull, A. E. S., 1949. J. Chem. Soc, 1101.Google Scholar
Campbell, N. and Wilson, N. H., 1970. Chemy Ind., 1114.Google Scholar
Collins, C. C. and Benjamin, B. M. 1953. J. Am. Chem. Soc, 75, 1644.Google Scholar
Courtot, Ch., 1915. Annls Chim., 4, 159.Google Scholar
Dickinson, J. D. and Eaborn, C., 1959. J. Chem. Soc, 2337.CrossRefGoogle Scholar
Kippenberg, H., 1897. Ber. Dt. Chem. Ges., 30, 1132.Google Scholar
Pfeiffer, P. and Roos, H. H., 1941. J. Prakt. Chem., 159, 13.CrossRefGoogle Scholar
Rieche, A., Gross, H. and Hoft, E., 1960. Chem. Ber., 93, 88.CrossRefGoogle Scholar
Tucker, S. H., 1949. J. Chem. Soc, 2182.CrossRefGoogle Scholar
Tucker, S. H., 1952. J. Chem. Soc, 803.CrossRefGoogle Scholar
Von, I. and Wagner, E. C., 1944. J. Org. Chem., 9, 155.CrossRefGoogle Scholar
Vorländer, D. and Prttzsche, A., 1913. Ber. Dt. Chem. Ges., 46, 1793.CrossRefGoogle Scholar
Wegscheider, R. and Hecht, J., 1903. Mh. Chem., 24, 413.Google Scholar