Journal of Organic Chemistry p. 4654 - 4657 (1982)
Update date:2022-07-30
Topics:
Rossi, Roberto A.
Palacios, Sara M.
Santiago, Ana N.
The photostimulated reaction of 1-bromoadamantane (1) with diphenylphosphide (2) and diphenylarsenide (6) ions in liquid ammonia afforded good yields of the substitution products, together with small amounts of adamantane (4) and 1,1'-biadamantyl (5) as byproducts.The reaction of 1 with 2 in the dark did not occur, but stimulation with solvated electrons gives a small amount of the substitution product and 5, with a large amount of 4.The photostimulated reaction of 1 with 2 is inhibited by p-dinitrobenzene and di-tert-butyl nitroxide.All these results suggest that these reactions occur by the SRN1 mechanism of substitution, where radical and radical anions are intermediates.
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