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Reactivity of (3-chloro-2-methylenecycloalkyl)palladium chloride dimers: palladium catalysed tropone formation

✍ Scribed by William A. Donaldson; Daniel J. Stepuszek

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
137 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

The formation of 4-(2', 3',4'-trim.ethoxyphenyl)-5-methyltropone from the pallacium catalysed ring opening--oxidation of 7-methylenebicyclo[4.l.O]heptane is described. 6e have recently shown that the chloropalladation of la affords a mixture of cycloheptyl x-aliyl complexes 2a and 2b.-a Furthermore, this mixture can be utiilzed, in a scoichiometric fashion, for the preparation of tropones reiated to the anrimltotlc agent colchlcrne ' This letter reports on a novel palladium catalysed preparatran of 44(2', 3',4'Ptrlmethoxyphenyl)-5-methyltropone (3). We have prevrously shown that the chloropalladatron of l-aryl-7-methylenebicyclo[4.1.0lheptanes ICH,Cl,, 23"C), which yields the isomeric (1-aryl)-and

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Reactivity of (3-chloro-2-methylenecyclo
Reactivity of (3-chloro-2-methylenecycloalkyl)palladium chloride dimers: pd-allyl cleavage, synthesis of (Β±)-13-methyltridecanolide.
✍ William A. Donaldson; Barbara S. Taylor πŸ“‚ Article πŸ“… 1985 πŸ› Elsevier Science 🌐 French βš– 250 KB

The reactions of the title compounds under cleavage conditions affords the corresponding cycloalkenes as the major product. This methodology was used in the synthesis of 13-methyltridecanolide from cyclododecene. The chloropalladation of Q-methylenebicyclo[n.l.O]alkanes (1) quantitatively affords cr

Reactivity of (3-chloro-2-methylenecyclo
Reactivity of (3-chloro-2-methylenecycloalkyl)palladium chloride dimers: Nucleophilic attack by one or two equivalents of malonate anion.
✍ William A Donaldson; Valerie J Grief πŸ“‚ Article πŸ“… 1986 πŸ› Elsevier Science 🌐 French βš– 296 KB

The title compounds undergo reaction with one and two equivalents of malonate anion in the presence of phosphine ligands to afford mono-and di-substituted products. A mechanism for the formation of both products is presented. We' and others' have recently shown that the chloropalladation of Q-methy