Carbonylation reactions: 8. Chlorocarbonylation reactions: catalytic formation of chloroacyl chlorides without phosgene and application to the synthesis of 2(H)-5-furanone

Chloroacyl halides are obtained under mild conditions by catalytic carbonylation in halogenated solvents of allylic halides or ethylene and allyl chloride mixtures under pressure of CO and anhydrous HCl in the presence of PdCl 2; excellent selectivities for dichloroacyl and chloroacyl derivatives ar...

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Bibliographic Details
Published inJournal of molecular catalysis. A, Chemical Vol. 143; no. 1; pp. 181 - 195
Main Authors Bonnet, Michel C., Carmona, Nathalie, Tkatchenko, Igor
Format Journal Article
LanguageEnglish
Published Elsevier B.V 1999
Elsevier [1995, Vol. 95, n° 1-janvier 2017, vol. 426, part B]
Subjects
Allyl halides
Catalysis
Chemical Sciences
Chloroacyl chlorides
Chlorocarbonylation
Ethylene
Palladium
Reaction mechanisms
Palladium
Chloroacyl chlorides
Chlorocarbonylation
Reaction mechanisms
Allyl halides
Ethylene
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Summary:Chloroacyl halides are obtained under mild conditions by catalytic carbonylation in halogenated solvents of allylic halides or ethylene and allyl chloride mixtures under pressure of CO and anhydrous HCl in the presence of PdCl 2; excellent selectivities for dichloroacyl and chloroacyl derivatives are achieved. Allyl chloride is partly consumed for the regeneration of palladium chloride. The product of oxidative addition of HCl to the oligomeric [Pd(CO)Cl] n formed in situ by reaction of CO on PdCl 2 is proposed as the first step towards the generation of the active species.
ISSN:1381-1169
1873-314X
DOI:10.1016/S1381-1169(98)00386-0