Cycloheptatriene and tropylium metal complexes. Part VIII. A study of directive effects in nucleophilic addition to substituted tricarbonyltropyliumchromiums

Abstract

The methoxy-group directs entering methoxide ion into the substituted (1 -) position but borohydride attacks chiefly at position 3. Results with malonate and phenyl-lithium are confused by side-reactions and low yields; methyl-lithium causes reductive displacement of the methoxy-group. The results are compared with the behaviour of the metal-free ligand. The methoxycarbonyl group directs methoxide, cyanide, and hydride into the adjacent 2-position, but in the last case some attack at the 4-position is also observed.