AROMATIC CYCLIZATIONS OF β-AMINOETHYL RADICALS AND α-CARBAMOYLMETHYL RADICALS. ORTHO-SUBSTITUTION VS. IPSO-SUBSTITUTION

Article abstract of DOI:10.3987/COM-90-5559

On being treated with Bu3SnH, the N-benzyl-N-(β-bromoethyl)sulfonamide (4) underwent a homolytic ortho-substitution reaction to give the tetrahydroisoquinoline (6).In contrast, the N-arylmethyl-α-chloroacetamides (10) afforded the ipso-substitution products (11).A similar treatment of the N-naphthylmethyl derivative (16) provided the spiro-γ-lactam (17).