Vilsmeier Formylation of para-Substituted tert-Anilines Results in Dibenzodiazocines or Quinazolinium salts: a Remarkable Example of the 't-Amino Effect'

Article abstract of DOI:10.1039/c39950001463

Formylation of para-substituted tert-anilines with various N-formylated sec-anilines in phosphoryl chloride results in ortho-formylation followed by cyclisation of the iminium salt to the adjacent tert-amino α-position by way of the 't-amino effect' giving dibenzo<1,5>diazocines; in a similar manner, with N-formylated sec-aliphatic amines, quinazolinium salts are formed while bulky formanilides give the expected ortho-formylated tert-aniline.

Full text of DOI:10.1039/c39950001463

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