Journal of Organic Chemistry p. 4609 - 4613 (1984)
Update date:2022-08-04
Topics:
Palacios, Sara M.
Santiago, Ana N.
Rossi, Roberto A.
1-Haloadamantanes and 9-bromotriptycene react under irradiation with diphenylphosphide and diphenylarsenide ions to give the substitution product in good yields. 1-Iodoadamantane (8) also reacts with disodium telluride and disodium selenide under irradiation to give di-1-adamantyl ditelluride and di-1-adamantyl diselenide, respectively. 9,10-Dibromotriptycene with diphenylphosphide gives a good yield of the disubstitution product.It seems that all these reactions occur by the SRN1 mechanism.Substrate 8 reacts under irradiation with carbanionic nucleophiles and diethyl phosphite ion, but the products are adamantane and 1,1'-biadamantyl rather than substitution products.These nucleophiles transfer an electron to 8 to form radical anions which fragment to 1-adamantyl radicals.The radicals are reduced or dimerized.In contrast, amide ions do not react with 8.The ease of the halogen nucleofugality is I > Br > Cl, the same as in the aromatic system.
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