A Mechanistic Study of the De-t-butylation Reaction of 2,5-Di-t-butyl-p-dimethoxybenzene in Acid Systems

Chem. J. Chinese Universities ›› 1994, Vol. 15 ›› Issue (5): 685.

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A Mechanistic Study of the De-t-butylation Reaction of 2,5-Di-t-butyl-p-dimethoxybenzene in Acid Systems

GONG Yue-Fa¹, ZHAO Cheng-Xue¹, JIANG Xi-Kui²

1. Department of Chemistry, Huazhoug University of Science and Technology, Wuhan, 430074;
2. Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai

Received:1993-05-27 Revised:1994-01-25 Online:1994-05-24 Published:1994-05-24

Abstract

Abstract: We have observed that the debutylation reaction can readily occur when 2,5-di-tbutyl-p-dimethoxybenzene (1) was mixed with perfluorocarboxylic acids or with AlCl₃CH₂Cl₂ system,but did not occur with aqueous HI or HBF₄ or absolute trichloroacetic acid.EPR observation shows that radical intermediates were generated in the former systems,but not in the latter case.Kinetic study indicates that the reaction of substrate 1 with trifluoroacetic acid behaves third-order kinetics,second in 1 and first in the acid.All the results reveal that an intrinsic relation may exist between the debutylation and the formation of the radical intermediates.

Key words: De-t-butylation, Single electron transfer, Perfluorocarboxylic acid, Substituted benzene radical cation

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GONG Yue-Fa, ZHAO Cheng-Xue, JIANG Xi-Kui. A Mechanistic Study of the De-t-butylation Reaction of 2,5-Di-t-butyl-p-dimethoxybenzene in Acid Systems[J]. Chem. J. Chinese Universities, 1994, 15(5): 685.

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A Mechanistic Study of the De-t-butylation Reaction of 2,5-Di-t-butyl-p-dimethoxybenzene in Acid Systems

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