Abstract
10-Phenoxyphenothiabismine 5,5-dioxide (2a) and related compounds 2b,c, the first example of an air-stable aryloxybismuthane whose bismuth−oxygen bond is not incorporated into a ring system, were synthesized and fully characterized. Substitution of the OAr group in 2 by phenols in solution revealed two substitution tendencies. The substitution with 2-methoxyphenol proceeded preferentially due to intramolecular coordination of the 2-methoxy oxygen atom with the bismuth atom in 10-(2-methoxyphenoxy)phenothiabismine 5,5-dioxide (2b). Furthermore, the substitution is more favorable with more acidic phenols, which is in accord with the apicophilicity observed at an apical position in hypervalent compounds. 10-(4-Methoxyphenoxy)phenothiabismine 5,5-dioxide (2c) was found to form 10-(4-methoxyphenoxy)phenothiabismine 5,5-dioxide·4-methoxyphenol 1:1 complex (3) through hydrogen bonding between the OH group of 4-methoxyphenol and the aryloxide oxygen atom of 2c. Such complex formation may be the initial step of th...
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