Electrophilic Aromatic Substitution. 6. A Kinetic Study of the Formylation of Aromatics with 1, 1-Dichloromethyl Methyl Ether in Nitromethane

Franklin P. Dehaan, Gerald L. Delker, William D. Covey, Anthony F. Bellomo, Julie A. Brown, Dato M. Ferrara, Richard H. Haubrich, Elliot B. Lander, Carol J. MacArthur, Rolf W. Meinhold, Diane Neddenriep, David M. Schubert, Robert G. Stewart

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Abstract

The reaction between 1, 1-dichloromethyl methyl ether (DOME), benzene or toluene, and aluminum chloride or titanium tetrachloride was studied in nitromethane solvent at-27 °C with vacuum line techniques and gas chromatography. For either aromatic the ratf law was first order in aromatic, in DOME, and in metal halide as catalyst. With both metal halides, kT/kB ratios and product isomer percentages are consistent with Brown's selectivity relationship. Aluminum chloride catalyzed decomposition of DOME was observed at higher temperatures. The side reaction probably invalidates earlier literature results.

Original languageEnglish (US)
Pages (from-to)3963-3966
Number of pages4
JournalJournal of Organic Chemistry
Volume49
Issue number21
DOIs
StatePublished - Oct 1984

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Dehaan, F. P., Delker, G. L., Covey, W. D., Bellomo, A. F., Brown, J. A., Ferrara, D. M., Haubrich, R. H., Lander, E. B., MacArthur, C. J., Meinhold, R. W., Neddenriep, D., Schubert, D. M., & Stewart, R. G. (1984). Electrophilic Aromatic Substitution. 6. A Kinetic Study of the Formylation of Aromatics with 1, 1-Dichloromethyl Methyl Ether in Nitromethane. Journal of Organic Chemistry, 49(21), 3963-3966. https://doi.org/10.1021/jo00195a016