Nitrenium ions. Part 4. Reactivity and crystal structure of 1-methyl-2-phenyl-3-N-benzoyloxyindole iminium perchlorate and reactivity of N,N-dimethylamino-p-N-benzoyloxyaniline nitrenium chloride with 2-phenylindole

1-Methyl-2-phenyl-3-nitrosoindole and N,N-dimethyl-p-nitrosoaniline react w ith benzoyl chloride to form salts behaving like iminium and nitrenium ions respectively. The structure of che ion formed in the case of the nitrosoin dole was elucidated by X-ray analysis. The charge density distribution of b oth ions was calculated on the basis of the structure parameters and by AM1 calculations and their reactivity was interpreted on the basis of structur al parameters and the calculated distribution of their positive charge.