Journal of Organic Chemistry p. 4959 - 4963 (1986)
Update date:2022-08-04
Topics:
Day, J. C.
Govindaraj, N.
McBain, D. S.
Skell, P. S.
Tanko, J. M.
The chemistries of 1,8-naphthalenedicarboximidyl (N.) and phthalimidyl (P.) radicals are described.Hydrogen abstractions from alkanes and additions to olefins and benzene proceed in high yield.The low cost of phthalimide, coupled with the absence of a parasitic ring-opening reaction for P., makes N-bromophthalimide an economical reagent for low-selectivity brominations.The chemistry of N. resembles that of other imidyl radicals (succinimidyl, glutarimidyl) with respect to selectivities.Conversely, P. is somewhat of a maverick among imidyl radicals, being slightly more selective in its reactions, but still 102-103 less selective than Br..
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