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Article: The aromatic character and resonance stabilization energies of substituted cyclopentadienyl and indenyl cations (1).
- Article from:
- Canadian Journal of Chemistry
- Article date:
- September 1, 2005
- Author:
CopyrightCOPYRIGHT 2005 NRC Research Press. This material is published under license from the publisher through the Gale Group, Farmington Hills, Michigan. All inquiries regarding rights should be directed to the Gale Group. (Hide copyright information)
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Introduction
We recently reported on the photochemistry of the indenyl esters, acetates (1a-1c) and pivalates (2a-2c), in both methanol and cyclohexane solvents (1). In cyclohexane, the products obtained were derived entirely from the radical pair intermediates expected from homolytic cleavage of the carbon-oxygen bond. In methanol, the methyl ethers 3a and 3b were obtained in significant yield (from 0% for 2a to 100% for 1c) as a consequence of the formation of ion-pair intermediates.
The mechanism of formation of ion-pair intermediates in photosolvolysis reactions has attracted considerable interest recently with two quite different pathways proposed. ...