ChemInform Abstract: REACTIONS OF A VARIETY OF DIAZOALKANES WITH O-SULFOBENZOIC ANHYDRIDE

It was found that a number of diazoalkanes (I) bearing a relatively small substituent reacted with o-sulfobenzoic anhydride (II) in acetonitrile at an ordinary temperature to give the o-(substituted glycoloyl)benzenesulfonic acid sultones (IV), which correspond formally to the products from the insertion into the C–O bond of II by the carbenes, while diaryldiazomethanes underwent decomposition under the same conditions to produce the corresponding tetraarylethylenes (V) instead of the inserted products (IV). The olefin formation reaction was very fast compared to the sultone formation and was considered to be the result of the acid-catalyzed decomposition caused by the contaminant o-sulfobenzoic acid (III) which was derived from II. The kinetics and the mechanism of these reactions were discussed on the basis of the nature of diazoalkanes.