Journal of the Chemical Society. Perkin transactions I p. 295 - 302 (1981)
Update date:2022-07-30
Topics: Reactants photochemical reactions Product Absorption Aliphatic amines Substituted benzenes
Gilbert, Andrew
Krestonosich, Stefan
Westover, David L.
The products arising from the irradiation of diethylamine and t-butylamine with toluene, chlorobenzene, anisole, benzonitrile, benzyl fluoride, benzotrifluoride (α,α,α-trifluorotoluene), m-fluorobenzotrifluoride (α,α,α,m-tetrafluorotoluene), p-fluorotoluene, m-fluorotoluene, p-fluoroanisole, m-fluoroanisole, and 1,3-bis(trifluoromethyl)benzene, and of triethylamine with toluene, benzotrifluoride and 1,3-bis(trifluoromethyl)benzene, all at 254 nm, are described.Reaction pathways involving both substitution and 1,2- and 1,4-acyclic addition processes are observed and which predominates depends upon the arene substituent.The novel acyclic adduct, Me2C=CH-CH=CH-CH=NBut, is obtained from toluene and t-butylamine and, contrary to previous reports, chlorobenzene yields arene-amine 1:1 adducts as well as the amine α-substitution product (16); benzonitrile gives aniline derivatives with the primary and secondary amines.
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