Abstract
Reaction of tricyclic azetidinones 1–5 (azetobenzoxazine, -thiazine, -thiazepine and -azepine derivatives) with trifluoroacetic acid led to bicyclic thioesters 6–13. There is evidence for an intermolecular reaction, a possible mechanism is discussed. The structure of two representative thioesters (8 and 9) was elucidated by different NMR experiments, complete assignments of 1H- and 13C-chemical shifts are given. Reaction of the azetobenzoxazine 2 with sodium periodate and magnesium monoperoxyphthalate led to the sulfoxide 18 and the sulfone 19, respectively.
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