Double arylation of vinyl allene skeleton in AlCl 3 -promoted transformation of (5-methylhexa-1,3,4-trien-3-yl)diphenylphosphine oxide in benzene
Abstract
The transformations of allenyl(diphenyl)phosphine oxide with a vinyl group at the α-carbon atom - (5-methylhexa-1,3,4-trien-3-yl)diphenylphosphine oxide 1 - were studied in the presence of Brønsted acids (TfOH, H2SO4, and HCl/dioxane), as well as in the presence of some Lewis acids - BF3·Et2O and AlCl3 in dichloromethane, and AlCl3 in benzene. It was found that if benzene was used as a solvent, the products of the double arylation could be isolated as two diastereomers in a 1/1 ratio in 73% overall yield.
Fields of Study & Subjects
Phosphorus compounds and reactions
Organophosphorus compounds synthesis
Organic and Inorganic Chemical Reactions
Publication details
- Journal / source
- Synthetic Communications
- Volume
- 56
- Issue
- 5
- Pages
- 428–436
- Publication date
- 1 March 2026
- Language
- EN