Dibenzothiepin derivatives and related compounds. V. Reactions of 6,11-dihydrodibenzo[b,e]thiepin 5-oxides with SbCl5 and perchloric acid.

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Abstract
Reactions of sulfides with SbCl5 or perchloric acid were examined. Sulfoxides having no α-hydrogens produced very stable 1 : 1 adducts of them and SbCl5. On the other hand, sulfoxides having α-hydrogens formed the intermediates of sulfonium or carbonium ion. In the reactions of benzyl phenyl sulfoxide (12) and 11-phenyl-6, 11-dihydrodibenzo-[b, e] thiepin 5-oxide (21a) the intermediates reacted with MeONa to give sulfides substituted by a methoxy group at α-position. A novel transannular reaction and an intramolecular 1, 2-rearrangement of the intermediate were found in the reaction of 11-phenyl-6, 11-dihydrodibenzo [b, e] thiepin-11-ol 5-oxide (26) or 11-methoxy-11-phenyl-6, 11-dihydrodibenzo [b, e] thiepin 5-oxide (34). The bridged sulfonium intermediate (32) was isolated in good yield from the reaction of 26 or 34 with perchloric acid. The mechanism of the reactions was discussed.

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