Evidence is presented that the only significant reaction of 2-methyl-2-propanesulfonyl chloride (1) (a) in water over the pH range 3.5-13.0 or (b) in methanol-chloroform-d is an ionization to the ieri-butyl cation (2) and the chlorosulfite anion (CISO2-), followed by further reactions of these species. The organic products include isobutylene (3), ieri-butyl chloride (4a), ieri-butyl alcohol (4b), and, at high pH, 2-methyl-2-propanesulfinate anion (6) and small amounts of 2-methyl-2propanesulfonate anion (5). In the presence of barium chloride the rate of hydrolysis of 1 is constant over the pH range 3.5-12.0.
2-Alkyl (or aryl) indoles react readily with phenylhydrazine in hydrochloric–acetic acid to give o-aminophenylpyrazoles 7, if the 2-substituent is of small or moderate size, or else 3-aminoindoles, if the 2-substituent is sufficiently bulky. The 3-aminoindoles readily undergo oxidative dimerization to indolylidene aminoindoles [Formula: see text] Evidence is provided for the mechanisms of formation of these two kinds of products.
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