Potassium tert-butoxide → 1-Ethynyladamantane

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The Stetter and Goebel reference, also cited above, discloses the synthesis of 1-ethynyladamantane from 1-bromoadamantane in good yield. We repeated that procedure with minor modifications by reacting 1-bromoadamantane with vinyl bromide in the presence of aluminum bromide to give the 2,2-dibromoethyl derivative, then dehydrobrominating that derivative in situ with potassium t-butoxide in triethylene glycol to give 1-ethynyladamantane in 60% overall yield.

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