0.412g 1,4-dichlorobutyne was dropped to a well stirred blue solution of
NaNH2 (0.50g Na, 14.1mmol, 4eq) in liquid ammonia under nitrogen at
-78oC to give a beige suspension which was stirred for 1h before
adding 1g (6.7mmol) adamantanone dissolved in 100ml ether and a trace of FeCl3.
The suspension then was allowed to reach roomtemperature while continously
replacing the evaporating ammonia with 100ml ether. The reaction mixture was
allowed to boil under reflux for 16h. The reaction was halted with excess of
ammoniachloride, and the usual work-up yielded a yellow oil that was passed
through a silica column (petrol/ethylacetate=1:1.5). Four components were
separated of which the last one with an RF=0.5 was found to be
1,4-bis-(2,2-hydroxyadamantyl)-diacetylene 8, m.p.>
300oC. MS, (m/z) 344 (M+NH4)+, 326 (M+), 309,
294, 281, 265, 251, 237, 228, 201, 191, 176, 168, 159, 151, 121, 107, 91, 55;
IR, 3278.7 (O-H), 2902.5, 2854.5, 2148.2 (C[[equivalence]]C) cm-1;
Crystals suitable for X-ray analysis were grown in chloroform/pentane.