However, boiling under reflux (160oC) for 1h in DMF nearly totally shifted the equilibrium of the two isomers towards the ethynyl compound (15). IR : 2926.0, 2164.1, 1687.4, 854.0 cm-1. The yellow oil was diluted with 80ml ethanol and slowly added to a saturated solution of ammonia in ethanol before stirring for 67h at roomtemperature. To complete the reaction, gaseous ammonia was bubbled through the to 60oC warmed solution for 4h. Basic work-up gave 1.4g (48%) of a yellow oil which contained at least 3 different substances (TLC: hexane/ether/ethylacetate/petrol =17.5:5:2.5:2.5). Desilylation in 20ml methanol containing excess potassium hydroxide at reflux for 1h gave a yellow oil consisting of 4 compounds, of which the one with RF=0.5 (hexane/ether/ethylacetate/ petrol =17.5:5:2.5:2.5) turned out to be 2-amino-2-ethynyl-adamantane 5 with 15% yield (0.31g). Crystals suitable for X-ray analysis were grown with the slow evaporation method.