As a fundamental study on dibenzothiepins, reaction of 11-phenyl-6, 11-dihydrodibenzo [
b
,
e
] thiepin-11-ol (10) or 11-chloro-11-phenyl-6, 11-dihydrodibenzo [
b
,
e
] thiepin (14) with triphenylmethyl cation or
SbCl5
was examined under various conditions. 11-Phenyl-6, 11-dihydrodibenzo [
b
,
e
] thiepin-11-ylium salt (8) was isolated as a black powder (perchlorate) and a green powder (hexachloroantimonate), but BF
4 salt was obtained only as a solution. Treatment of the hexachloroantimonate with excess of
SbCl5
was found to result in a novel dehydrocyclization reaction to give selectively
9
, 13
b
-dihydrofluoreno [
1
,
9
a,
9
-c, d] [2]-benzothiepin-13
b
-ylium hexachloroantimonate (19). Some discussions were made on the mechanism of the formation of 19.
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