Cleavage of 2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-2-phenyl-1,3-dithianes with HgO/BF3

Article abstract of DOI:10.1007/BF00806969

The title compounds (5) were prepared by addition of 2-phenyl-1,3-dithiane anion (2-lithiated 10) to adequately substituted N-alkyl-3,4-dihydroisoquinolinium salts (7a-7g). Cleavage of compounds 5 with HgO/BF₃ affords S-benzoyl-1,3-propanedithiol (4a) and the corresponding disulfide 4c, benzaldehyde, and Hg(I) ions. In contrast to the title compounds, 2-(α-dialkylaminobenzyl)-2-phenyl-1,3-dithianes (6) yield benzil under these conditions.