Dihydroisochinolinumlagerung, 38. Mitt. Verhalten von 1,2-Dihydroisochinolinen mit sperrigen C-1-Substituenten gegen Säuren

Rearrangement of Dihydroisoquinolines, XXXVIII: Behavior of 1,2-Dihydroisoquinolines with Bulky C-1-Substituents towards Acids The 1,2-dihydroisoquinolines 2a-2d , obtained from the iminium salts 1a-1d by reduction with LiAlH₄, are heated with dilute acids. The dihydroisoquinolines 2a and 2b rearrange with yields of 44% to 3a and 3b, 2c with a yield of 17% to 3c. Compound 2d does not rearrange, 70% of it are recovered. As an elimination product of the reaction of 2b with 0.1N HCl, 2,2′-ethane- 1,2-diylbisnaphthalene (12) was found which probably is a recombination product of β-naphthylmethyl radicals.