127086-64-0Relevant articles and documents
Reactions of halo- and dihaloadamantanes with nitromethane anions by the SRN1 mechanism
Santiago, Ana N.,Toledo, Carlos A.,Rossi, Roberta A.
, p. 413 - 419 (2007/10/03)
The reactions of 1-bromo-, 2-bromo-, 1,3-dibromo- and 1, 4-dibromoadamantane with -CH2NO2 anions were studied in DMSO and in liquid ammonia. The photostimulated reaction of 1-haloadamantane (1-AdX, X = Br, I) or 2-AdBr with -CH 2NO2 anions gave good yields of the substitution product 1-AdCH2NO2 and 2-AdCH2NO2, respectively, in the presence of the enolate anions of acetone (entrainment conditions). On the other hand, 1-adamantanol was the main product of the reaction performed in DMSO without irradiation, but not in liquid ammonia. 1,3-Dibromo and 1,4-dibromoadamantane reacted with -CH 2NO2 anions under irradiation in the presence of the enolate anions of acetone. The first compound gave the disubstitution product 11, and the second the monobromo-substitution products 15 and 16, together with the disubstitution product 17. Compounds 15 and 16 were shown to be intermediates in the formation of 17. Copyright
