On reaction with N,N-dichloro-t-butylamine or -cyclohexylamine in benzene at 0 "C, nickel tetracarbonyl evolves three moles of carbon monoxide per mole. A colorless precipitate ( I ) is formed that has a Ni:N ratio of 1 : 1 and is insoluble in the usual solvents. 2 RNClz + 2 Ni(CO)4 + 2 [RNClzNi(CO)] (1) HzO -lmoleH 0 excess of H 0 ~ 5 2 RNHz + 2 NiClz + 2 COz ~-RHN-CO-NHR + 2 NiCIz + COz Addition of the complex ( I ) to water gives equimolar amounts of the original amine and nickel(l1) chloride (carbon dioxide was determined qualitatively). However, cautious hydrolysis of ( I ) with moist benzene or moist diethyl ether permits isolation of the N,N'-dialkylurea in yields of 80 % calculated on the amount of nickel carbonyl that reacted; the stoichiometric amount of nickel(I1) chloride remains on evaporation of the reaction mixture. Cautious deuteriolysis E 300 Raman 500 L 300 Raman 500 especially on derivatives o f ethane and cyclohexane [I].
However, no studies have been carried out on molecules in which two aliphatic rings are linked by a single bond. We have therefore commenced a systematic investigation of the conformations of the compounds in the homologous series in order to find out whether these compounds show rotational isomerism around the central C-C single bond and to determine the extent to which this isomerism depends on the strain in the rings, the spatial requirements of the rings, and the hybridization of the two central carbon atoms.
The following observations on bicyclopropyl were made: