Journal of the Chemical Society. Perkin transactions II p. 1895 - 1900 (1995)
Update date:2022-08-11
Topics:
Albini, Angelo
Siviero, Enrico
Mella, Mariella
Long, Conor
Pratt, Albert
Irradiation of 1,4-dimethoxynaphthalene (DMNH) in the presence of 4-substituted benzyl chlorides (X-C6H4CH2Cl, X=H, Cl, CN or NO2) in the either acetonitrile or benzene solution results in benzylation of DNNH, predominantly at position 2 and to a lesser extent on the unsubstituted ring.Steady-state and flash photolysis studies show that charge transfer between singlet excited DMNH and the chlorides is involved.The reaction occurs predominantly in-cage via concerted electron transfer and carbon-chlorine bond cleavage with X=H or Cl, while with X=NO2 fragmentation of the benzyl chloride radical anion occurs out-of-cage, but the process in this case is much less efficient due to competing back electron transfer.
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