102493-54-9

Upstream product

• 3029-30-9 naphthalene-1,4-dicarbonitrile 
• 101-81-5 Diphenylmethane 
• 632-50-8 1,1,2,2-tetraphenylethane 

Downstream Products

• 3029-30-9 naphthalene-1,4-dicarbonitrile 
• 95065-55-7 1-(4-Methoxy-benzyl)-1,2-dihydro-naphthalene-1,4-dicarbonitrile 
• 95065-53-5 4-(3'-fluorobenzyl)-1-naphtalenedicarbonitrile 
• 98689-34-0 3-Benzylnaphthalene-1-carbonitrile 
• 83242-06-2 2-benzyl-1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 78075-59-9 4-benzyl-1-naphthalenecarbonitrile 
• 83242-05-1 1-Benzyl-1,2-dihydro-1,4-naphthalenedicarbonitrile 

Relevant academic research and scientific papers

Set Photochemical Reactions between 1,4-Naphthalenedicarbonitrile and Benzylic Donors. Medium Effects

The electron transfer induced photochemical reactions 1,4-naphthalenedicarbonitrile (NDN) with toluene (1a), diphenylmethane (1b), p-methoxytoluene (1c), and benzyltrimethylsilane (1d) in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN were examined.The results were compared with those of reactions occurring in neat MeCN.Under the former conditions, the cation radical derived from 1a undergoes deprotonation after diffusion from (rather than within) the geminate ion pair (as in MeCN).The formed benzyl radical abstracts a hydrogen from MeOH leading to hydroxymethylation of NDN competitively with its benzylation.Under basis conditions MeO(-) adds to 1a(+.) yielding 1c.The reaction of 1b in MeOH-MeCN and 0.1 M KOH-MeOH-MeCN is similar to that of 1a.However, in the reaction of 1c under these conditions, the arene cation radical undergoes deprotonation out of cage.Finally, desilylation of the cation radical from 1d is a fast process occurring from the geminate pair in all the media explored.

Photochemical Reaction between 1,4-Naphthalenedicarbonitrile and α-Substituted Benzylic Derivatives

The photochemical reaction of 1,4-naphthalenedicarbonitrile (NDN) with benzylic derivatives of the general formula PhCHRX (R = H, Ph; X = H, C, O, S, Si, Sn-bonded substituents) has been investigated.The competition between C-H and C-X bond cleavage in the photochemically created radical cation PhCHRX(.+) is revealed by the different chemical products formed, viz. 5,11-methanodibenzocyclooctenes (2), from proton transfer and coupling of the radicals within the cage, and 2-benzyl- (3) and 1-benzyl-1,2-dihydronaphthalenes (4), as well as 4-benzyl-1-naphthalenenitriles (5), from the reaction between the radical anion NDN(.-) and the neutral radicals PhCHR(.) or PhCRX(.).With the alcohols, the hydroxylic proton is easily transferred.Measurement of reaction quantum yield and fluoroscence quenching and thermochemical calculations support the mechanism proposed.

Photochemical Reaction of 1,4-Naphthalenedicarbonitrile with Alkylbenzenes and Bibenzyls

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.