Ipso nitration. A study of the migratory aptitude of ... - ACS Publications

A study of the migratory aptitude of the nitro group in the 1,2-dimethyl-1-nitrocyclohexadienyl cation. Craig E. Barnes, and Philip C. Myhre. J. Am. C...
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Communications to the Editor

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in dry n-hexane, 1-2% in HOAc, and -8% in ethanol. (9) C. L. Perrin, J. Am. Chem. SOC.,99, 5516 (1977). (IO) V. P. Vitulloand N.Grossman. J. Am. Chem. SOC.,94, 3844(1972).

Craig E. Barnes, Philip C. Myhre* Departnient of Chemistry, Haroey M u d d College Claremont, California 9 / 7 1 I Receiced October 12, I977

Ipso Nitration. A Study of the Migratory Aptitude of the Nitro Group in the 1,2-Dimethyl-l-nitrocyclohexadienylCation Sir:

Trapping studies indicate that the ipso ion, 1,2-dimethyl1 -nitrocyclohexadienyI cation ( l ) ,is formed in >50% yield upon nitration of 1,2-dimethylben~ene.I~~ Ion 1 is known to

dimethyl-4-nitrobenzene could be detected with detection limits of