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1-Bromoadamantane is an important intermediate, used in synthesizing medicines and new materials etc.
SL Regen .; JJ Besse .; J McLick. Solid-phase cosolvents. Triphase catalytic hydrolysis of 1-bromoadamantane. Journal of the American Chemical. 1979 101, (1), 116-120.
SL Regen.; L Dulak. Solid-phase cosolvents. Journal of the American Chemical society. 197799, (2), 623-625.
Reduction with Tri-n-butyltin hydride, A13298, generates the 1-adamantyl radical which, e.g. adds to Michael acceptors in good yield: J. Org. Chem., 53, 1285 (1988).
With activated Ca metal (prepared from CaBr2 and Li biphenylide), forms an organocalcium reagent which reacts with ketones to give tertiary alcohols; the preparation and reactivity of these intermediates is discussed: Org. Synth. Coll., 9, 9 (1998).
Undergoes Heck-type coupling with styrenes and arenes, catalyzed by Pd on carbon: Synthesis, 148 (1998).