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

doi:10.1021/jo00195a016

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

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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, k_T/k_B 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 language	English (US)
Pages (from-to)	3963-3966
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	49
Issue number	21
DOIs	https://doi.org/10.1021/jo00195a016
State	Published - Oct 1984
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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

Dehaan, FP, Delker, GL, Covey, WD, Bellomo, AF, Brown, JA, Ferrara, DM, Haubrich, RH, Lander, EB, MacArthur, CJ, Meinhold, RW, Neddenriep, D, Schubert, DM & Stewart, RG 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, vol. 49, no. 21, pp. 3963-3966. https://doi.org/10.1021/jo00195a016

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

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.",

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

year = "1984",

month = oct,

doi = "10.1021/jo00195a016",

language = "English (US)",

volume = "49",

pages = "3963--3966",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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AU - Dehaan, Franklin P.

AU - Delker, Gerald L.

AU - Covey, William D.

AU - Bellomo, Anthony F.

AU - Brown, Julie A.

AU - Ferrara, Dato M.

AU - Haubrich, Richard H.

AU - Lander, Elliot B.

AU - MacArthur, Carol J.

AU - Meinhold, Rolf W.

AU - Neddenriep, Diane

AU - Schubert, David M.

AU - Stewart, Robert G.

PY - 1984/10

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N2 - 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.

AB - 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.

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

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