DL CAMPHOR 3-SULFONIC ACID AND OTHER KETO α-SULFONIC ACIDS

Abstract

Sulfur trioxide-dioxan reagent has been used to convert acetophenone, 4-t-butylcyclohexanone, DL camphor and menthone to the α-sulfonic acids (3, 5, 2 and 12). Attempts to convert 3, 5 and 12 to the corresponding sulfonyl chlorides were unsuccessful. However, camphor-3-sulfonyl chloride (6) was obtained, and was characterized as the amides (7–10) and the N-phenylhydrazide (11). With chlorosulfonic acid, 3 afforded the 2ω-disulfonyl chloride (4). The mechanism of α-sulfonation is briefly discussed together with the spectral data and results of preliminary biological screening