removed in vacuo the residue was bulb to bulb distilled 90 u00b0 c 0 5 mmhg to afford 13 9 g 88 of the desired product as a colorless liquid ftir thin film 2962 1559 1419 1364 1168 cm u2212 1 1 h nmr 300 mhz cdcl 3 u03b4 1 30 s 9h 2 77 s 3h 7 10 t j 4 7 hz 1h 7 79 d j 7 7 hz 1h 8 47 d j 4 4 hz 1h 13 c nmr 75 mhz cdcl 3 u03b4 24 3 30 8 isomer 31 0 47 7 120 9 123 0 isomer 128 5 144 7 isomer 146 0 149 0 156 3 isomer 163 7 hrms calcd for c 10 h 16 ns m h 182 1003 found 182 1006 m h to a three necked flask equipped with a mechanical stirrer was added thf 200 ml n buli 17 4 ml 43 5 mmol 2 5 m in hexane and isopropylamine 5 7 ml 43 5 mmol at u2212 78 u00b0 c after 30 minutes compound 4 7 1 g in 20 ml thf 39 5 mmol was added dropwise after stirring for 15 minutes cystamine 2 7 2 g in 20 ml dme 47 3 mmol was added in one portion the mixture was warmed to rt slowly and stirred overnight it was poured into water.