Potassium phthalimide (0.01 mol) + p-bromobenzonitrile (A) (0-01 mol) or p-bromonitrobenzene (B) (0.01 mol) + catalyst (0.01 mol) in solvent (100 nil), 24 h under nitrogen ArN(C0) ,C,H, Catalyst and solvent Yield (yo) (A) CuI, dimethylacetamide a 94 (A) Cu,O, dimethylacetamide 57 (A) C U ~+ , ~ dimethylacetamide a 55 (A) CuBr,, dimethylacetamide 12 (A) No catalyst, dimethylacetarnide a 8 (A) CuBr, dimethylacetamide a 82 (A) Cu, dimethylacetamide a 15 Temp. Catalyst and solvent ("C) CuI, dimethylacetamide 165 CuI, 2,4,6-collidine b 165 CuI, quinoline b 165 CuI, nitrobenzene 6 165 CuI, diethylene glycol dimethyl 162 Cur, dimethylformamide a 155 CuI, p-xylene 138 CuI, 2-picoline 0 128* For recent discussions of copper-assisted nucleophilic substitutions involving perfluoro-aryl and -alkyl halides see

The 13C n.m.r. data of a variety of substituted adamantanes, diamantanes, and triamantanes are presented. The cc-substituted chemical shifts (SCS) can be described by gauche XC interactions, the magnitudes of which decrease in the sequence BrC > HC > OC 2 CC. Similarly, gauche interactions of the types HX and CX contribute to the (3-SCS. but additionally the (3-SCS are increased, if the a-carbon atoms possess antiperplanar y'-carbon atoms. Steric interaction of the substituent with gauche y-carbon atoms seem to cause rather downfield rather than upfield shifts of the y-signals. The hyperconjugative interaction of parallel C,-Cb-and Cg-C,<-bond orbitals increase the y,,,ii-SCS of the hydroxy and, to a smaller extent, the bromine substituent.

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The isomerisation of 2-methyladamantan-2-01 in 96% sulphuric acids over a wide range of temperatures,2 this is certainly not the situation in some other acidic media. Geluk acid has also been reported by H. W. Geluk and J. L. M. A.