Irradiation of 1,4-dicyanonaphthalene (DCN) and benzyl methyl ether gives the two diastereoisomeric 1-substituted 1,2-dihydronaphthalenes. A stereochemical assignment for these products, and related diastereoisomers pairs is proposed. The reaction occurs via the free radical ions and the low quantum efficiency is due to the slow deprotonation of the radical cation, with only moderate salt effect. In accordance with this scheme, the reaction with benzyl l-menthyl ether gives a low enantiomeric eccess.
The Photochemical-reaction Between 1,4-dicyanonaphthalene and Benzyl Ethers
TOMA, LUCIO;ALBINI, ANGELO
1991-01-01
Abstract
Irradiation of 1,4-dicyanonaphthalene (DCN) and benzyl methyl ether gives the two diastereoisomeric 1-substituted 1,2-dihydronaphthalenes. A stereochemical assignment for these products, and related diastereoisomers pairs is proposed. The reaction occurs via the free radical ions and the low quantum efficiency is due to the slow deprotonation of the radical cation, with only moderate salt effect. In accordance with this scheme, the reaction with benzyl l-menthyl ether gives a low enantiomeric eccess.File in questo prodotto:
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