95065-55-7Relevant academic research and scientific papers
Set Photochemical Reactions between 1,4-Naphthalenedicarbonitrile and Benzylic Donors. Medium Effects
Fasani, E.,d'Alessandro, N.,Albini, A.,Mariano, P. S.
, p. 829 - 835 (2007/10/02)
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 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
