Abstract
AbstractSome 5H,7H‐dibenzo[b,g][1,5]dithiocin oxides (4–8) and their related compounds 9–13 were prepared and the assignment of the most favorable conformation was carried out on the basis of the characteristic 1H NMR spectral data. Only a single conformer (BC: boatchair form) exists for 4,5, and 8–13, while two conformers (BC and TB: twist‐boat form) are apparent for 6 and 7. Oxidation and methylation of 4 gave exclusively a single geometrical isomer (8 and 13, respectively). These results are interpreted as a sterically preferential attack of electrophiles on the BC conformer of the starting material. A 1,5‐oxygen shift of 4 occurred smoothly to give 6 in the presence of trifluoroacetic acid in CDCl3 solution. The mechanistic investigation is described briefly. Differences in chemical behavior between dibenzodithiocin 12‐oxide 4 and dibenzothiazocine 12‐oxide 2 are also discussed on the basis of the conformational features.
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