83242-05-1

Basic information

• Product Name: 1,4-Naphthalenedicarbonitrile, 1,2-dihydro-1-(phenylmethyl)-
• CAS NO: 83242-05-1
• Molecular Formula: C19H14N2
• Molecular Weight: 270.334
• Mol File: 83242-05-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,4-Naphthalenedicarbonitrile, 1,2-dihydro-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Naphthalenedicarbonitrile, 1,2-dihydro-1-(phenylmethyl)-(83242-05-1)
• EPA Substance Registry System: 1,4-Naphthalenedicarbonitrile, 1,2-dihydro-1-(phenylmethyl)-(83242-05-1)

Safety Data

• Hazardous Substances Data: 83242-05-1(Hazardous Substances Data)

Upstream product

• 102505-27-1 1-(Diphenylmethyl)-1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 102493-54-9 cis-2-(1,1-Diphenylmethyl)-1,2-dihydro-1,4-naphthalenedicarbonitrile 
• 3029-30-9 naphthalene-1,4-dicarbonitrile 
• 108-88-3 toluene 
• 67-56-1 methanol 
• 107-13-1 acrylonitrile 
• 28493-54-1 benzyltributyltin 
• 2945-41-7 triethylgermylmethylbenzene 
• 770-09-2 benzyltrimethylsilane 
• 768-56-9 4-Phenylbut-1-ene 
• 766-92-7 [(methylthio)methyl]-benzene 

Downstream Products

• 78075-59-9 4-benzyl-1-naphthalenecarbonitrile 

Relevant articles and documents

Characterization of methylenepropenylidenecyclohexadiene derivatives and their competing 1,6-electrocyclic reaction and 1,7-hydrogen at room temperature

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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.

The Photochemical Reaction between 1,4-Dicyanonaphthalene and benzyl ethers

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 1-menthyl ether gives a low enantiomeric eccess.