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, Daro M. Ferrara, Richard H. Haubrich, Elliot B. Lander, Carol Macarthur, Rolf W. Meinhold, Diane Neddenriep, David M. Schubert, Robert G. Stewart

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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°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.

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

Fingerprint

Methyl Ethers
Metal halides
Substitution reactions
Kinetics
Toluene
Benzene
Isomers
Gas chromatography
Vacuum
Decomposition
Catalysts
nitromethane
Temperature
aluminum chloride

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., ... 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.

Electrophilic aromatic substitution. 6. A kinetic study of the formylation of aromatics with 1,1-dichloromethyl methyl ether in nitromethane. / DeHaan, Franklin P.; Delker, Gerald L.; Covey, William D.; Bellomo, Anthony F.; Brown, Julie A.; Ferrara, Daro M.; Haubrich, Richard H.; Lander, Elliot B.; Macarthur, Carol; Meinhold, Rolf W.; Neddenriep, Diane; Schubert, David M.; Stewart, Robert G.

In: Journal of Organic Chemistry, Vol. 49, No. 21, 1984, p. 3963-3966.

Research output: Contribution to journalArticle

DeHaan, FP, Delker, GL, Covey, WD, Bellomo, AF, Brown, JA, Ferrara, DM, Haubrich, RH, Lander, EB, Macarthur, C, 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.
DeHaan, Franklin P. ; Delker, Gerald L. ; Covey, William D. ; Bellomo, Anthony F. ; Brown, Julie A. ; Ferrara, Daro M. ; Haubrich, Richard H. ; Lander, Elliot B. ; Macarthur, Carol ; Meinhold, Rolf W. ; Neddenriep, Diane ; Schubert, David M. ; Stewart, Robert G. / Electrophilic aromatic substitution. 6. A kinetic study of the formylation of aromatics with 1,1-dichloromethyl methyl ether in nitromethane. In: Journal of Organic Chemistry. 1984 ; Vol. 49, No. 21. pp. 3963-3966.
@article{d239022c4206438ebec54dd9828b3d0e,
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 (DCME), 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 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.",
author = "DeHaan, {Franklin P.} and Delker, {Gerald L.} and Covey, {William D.} and Bellomo, {Anthony F.} and Brown, {Julie A.} and Ferrara, {Daro M.} and Haubrich, {Richard H.} and Lander, {Elliot B.} and Carol Macarthur and Meinhold, {Rolf W.} and Diane Neddenriep and Schubert, {David M.} and Stewart, {Robert G.}",
year = "1984",
language = "English (US)",
volume = "49",
pages = "3963--3966",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - Electrophilic aromatic substitution. 6. A kinetic study of the formylation of aromatics with 1,1-dichloromethyl methyl ether in nitromethane

AU - DeHaan, Franklin P.

AU - Delker, Gerald L.

AU - Covey, William D.

AU - Bellomo, Anthony F.

AU - Brown, Julie A.

AU - Ferrara, Daro M.

AU - Haubrich, Richard H.

AU - Lander, Elliot B.

AU - Macarthur, Carol

AU - Meinhold, Rolf W.

AU - Neddenriep, Diane

AU - Schubert, David M.

AU - Stewart, Robert G.

PY - 1984

Y1 - 1984

N2 - 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°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.

AB - 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°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.

UR - http://www.scopus.com/inward/record.url?scp=5344266024&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=5344266024&partnerID=8YFLogxK

M3 - Article

VL - 49

SP - 3963

EP - 3966

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 21

ER -