Formation of the Intermediate Methoxychloromethylene in the Reaction of Dichloromethyl Methyl Ether with Base

Journal Article · Thu Dec 01 04:00:00 EST 1960 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja01508a037· OSTI ID:4109404

Hine, Jack; Rosscup, Robert J.; Duffey, Donald C.

S>Comparisons of the rate of reaction of potassium isopropoxide with CHCl₂OCH₃ and CDCl₂OCH₃ showed a marked deuterium kinetic isotope effect (k_H/k_D = 5.4 2.2). This shows that the reaction involves an initial alpha -dehydrochlorination to give the intermediate methoxychloromethylene. In other experiments, potassium thiophenoxide was found to be about as reactive as potassium isopropoxide toward dichloromethyl methyl ether.

• Research Organization: Georgia Inst. of Technology, Atlanta
• Sponsoring Organization: USDOE
• NSA Number: NSA-15-008607
• OSTI ID: 4109404
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 23 Vol. 82; ISSN 0002-7863
• Publisher: American Chemical Society (ACS)
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ALKENES
ALKOXY RADICALS
CHEMICAL REACTIONS
CHLORINATED HYDROCARBONS
CHLORINATION
DEUTERIUM COMPOUNDS
ETHERS
HETEROCYCLICS
ISOMERS
ISOTOPE EFFECTS
MECHANICS
METHOXY RADICALS
METHYL RADICALS
METHYLENE
METHYLENE RADICALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
POTASSIUM OXIDES
PROPYL RADICALS
THIOPHENE