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

DOI: 10.1021/jo00195a016

Source and publish data:

Journal of Organic Chemistry p. 3963 - 3966 (1984)

Update date:2022-08-15

Topics:

Authors:

DeHaan, Franklin P.

Delker, Gerald L.

Covey, William D.

Bellomo, Anthony F.

Brown, Julie

et al. et al.

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Article abstract of DOI:10.1021/jo00195a016

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