127086-64-0Relevant academic research and scientific papers
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
The Photostimulated Reaction of 1-Iodoadamantane with Carbanionic Nucleophiles in DMSO by the SRN1 Mechanism
Borosky, Gabriela L.,Pierini, Adriana B.,Rossi, Roberto A.
, p. 3705 - 3707 (2007/10/02)
1-Iodoadamantane (1) reacts under irradiation with the enolate ions of acetone (2), acetophenone (5a), and propiophenone (5b) to give adamantane and the substitution products in variable yields.The anion of nitromethane (7) does not react under irradiation with 1, but excellent yields of 1-adamantylnitromethane (8) are obtained in the photostimulated reaction of 1 and 7 in the presence of 2 or 5a (entrainment reactions).We suggest that 1-iodoadamantane reacts with these nucleophiles by the SRN1 mechanism of nucleophilic substitution.
