95065-56-8Relevant academic research and scientific papers
Photochemical Reaction of 1,4-Naphthalenedicarbonitrile with Alkylbenzenes and Bibenzyls
Albini, Angelo,Fasani, Elisa,Mella, Mariella
, p. 4119 - 4125 (2007/10/02)
The photochemical reaction of 1,4-naphthalenedicarbonitrile with some alkylbenzenes and bibenzyls has been examined.A unitary mechanistic picture is formulated on the basis of product study, deuteration experiments, and fluorescence and reaction quantum yield measurements.Proton transfer within the singlet radical ion pair followed by in-cage cycloaddition of the two radicals yields stereoselectively 5,11-methanodibenzo cyclooctene derivatives (8).Reaction of benzyl radicals (formed by protolysis or, for radical cations having no benzylic proton, by C-C bond cleavage) with unprotonated NDN.- leads, again stereoselectively, to 2-benzyl-1,2-dihydronaphtalenes (9).Escape of the donor radical cation and following C-H or C-C bond cleavage leads to a different product, thus, benzyl radicals are trapped by NDN to yield substitution products (11) or recombine.Benzyl cations are trapped by nucleophiles.
The Effect of Substituents on the Photochemical Reaction between Naphtalenedicarbonile and Methylbenzenes
Albini, Angelo,Fasani, Elisa,Montessoro, Ezio
, p. 1409 - 1415 (2007/10/02)
The photochemical reaction between 1,4-naphtalenedicarbonile (NDN) and toluene in acetonitrile is extended to bibenzyl (4), 3- and 4-fluorotoluene (8, 7), and 3- and 4-methoxytoluene (9, 10).The product distribution obtained with compounds 4, 7 and 10 is
