Abstract
The photochemical reactions of acrylonitrile (1 ) with 1,5-dimethoxynaphthalene (2 ), 1-methoxynaphthalene (3 ) and 1,4-dimethoxynaphthalene (4 ) in various solvents have been investigated. In polar solvents (methanol and acetontrile), an electron transfer pathway leads to the formation of aromatic substitution (with 2 and 3 ) and addition products (with 4 ). In benzene, an exciplex-mediated [2π + 2π] cycloaddition occurs. The cycloadducts formed undergo a further photoinduced rearrangement via a [2σ + 2σ] cycloreversion followed by an intramolecular [4π + 2π] cycloaddition.
Key words
photochemistry - electron transfer - alkylations - cycloadditions - rearrangements
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