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A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes
Published on: February 27, 2017
On the addition of 4-(N,N-dimethylamino)phenyl cation to norbornene
Mariella Mella1, Maurizio Fagnoni, Angelo Albini
1Dept. Organic Chemistry, University of Pavia, v. Taramelli 10, 27100, Pavia, Italy.
Abstract:
The photochemically generated 4-(N,N-dimethylamino)phenyl cation adds to norbornene giving a phenylnortricyclene and various 2-exo substituted phenylnorbornanes (main isomers, 3-endo-, 7-anti- and 7-syn-phenyl). Acetamides are obtained in MeCN and ethers in alcohols (MeOH, iso-PrOH, tert-BuOH, CF3CH2OH). The product distribution is closely reminiscent of that obtained in the solvolysis of 2-norbornyl derivatives, supporting that the reaction offers a novel access to a 'non classical' 2-norbornyl cation. The fate of this cation is determined by the basicity/nucleophilicity of the solvent.
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