To a solution of 5.16ml 1.6M BuLi (8.26mMol) in 100ml ether was added dropwise
a solution of 0.4g (4.12mmol) 1,2-dichlorethylene in 20ml ether at
-78oC under nitrogen. The solution was allowed to reach room
temperature and then was stirred for 30 minutes to give a white suspension.
O.5g adamantanone in 50ml ether and a trace of FeCl3 were added over 30 minutes
before carefully heating to reflux for 30 minutes to turn immediately to a grey
suspension. After cooling down to room temperature the reaction mixture was
poured on ice-cold hydrochloric acid, extracted with ether and dried over
potassium carbonate, to give 0.6g (85%) of a white-yellow compound, m.p.
115-117oC. TLC (hexane/petrol/ethylacetate=1:1:1) yielded one single
spot, RF=0.5; IR (nujol) 3605.8, 3317.9 (O-H), 2907.8, 2857.9, 2222.1
(C[[equivalence]]C), 796 (C-Cl) cm-1; MS (m/z) 228
(M+NH4)+, 210 (M+), 193, 182, 174, 147, 105, 91. Crystals
suitable for X-ray analysis were grown in chloroform/pentane using the slow