3-(4-Methoxyphenoxy)-1,2-benzisothiazole 1,1-Dioxide: its Relation to Mechanistic Behaviour in Catalytic Transfer Hydrogenolysis

Conjugation of oxygen with an aromatic ring, as in a phenol, gives a C-O bond length of about 1.35 Å, whereas the C-O bond length in an aliphatic alcohol is about 1.45 Å. A saccharyl ether derivative of a phenol changes the phenolic C-O bond length to 1.42 Å and makes the bond chemically more susceptible to catalytic ipso replacement of the aromatic C-OH linkage by C-H. The present study of the title compound, C₁₄H₁₁NO₄S, was carried out in order to examine specifically the effect of saccharyl ether formation on the C-O bond length of a phenol.

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