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Isoerization of allylic acetates catalyzed by palladium. New method for stereocontrol.

✍ Scribed by Barry M. Trost; Thomas B. Verhoeven; Joseph M. Fortunak; Samuel M. McElvain

Book ID
104245039
Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
202 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction of allylic acetates with tetrakis (triphenylphosphine) Dnlladiumleadsto oositional and stereochemical isomerism.

A mechanism is proposed.

Elimination of ally1 acetates to dienes is also observed and constitutes a u efu synthetic procedure. The use of bis(benzenesulfonyl)methane as a 'CH2& equivalent is reported.

πŸ“œ SIMILAR VOLUMES

Palladium-catalyzed phenylation of allyl
Palladium-catalyzed phenylation of allylic acetates by tetraphenylborate anion
✍ Jean-Yves Legros; Jean-Claude Fiaud πŸ“‚ Article πŸ“… 1990 πŸ› Elsevier Science 🌐 French βš– 235 KB

Commercial sodium tetraphenylborate is a convenient phenylating reagent in the palladium(O)-catalyzed substitution of allylic acetates. Two phenyl groups of NaBPh4 are available for transfer. Triphenylboron is also a phenylating agent in this reaction. We report here the use of sodium tetraphenylbo