ANOMALOUS REACTIONS IN ATTEMPTS TO PREPARE 3-ALKYLTHIOINDOLES
- 1 May 1965
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 43 (5) , 1298-1305
- https://doi.org/10.1139/v65-177
Abstract
Indole magnesium bromide reacting with ethanesulfenyl chloride produces ethyl mercaptan, diethyl disulfide, indole, 3-ethylindole, 3-ethylthioindole, and 3,3′-diindolyl sulfide, along with at least three compounds not yet identified.The reaction of ethyl mercaptan with N-benzoyl-3-bromoindole in dimethylformamide containing potassium carbonate produces indole, 3-bromoindole, ethyl thiolobenzoate, 3-ethylindole, diethyl disulfide, and 3-ethylthioindole.In both of these reactions a substance (or substances) which caused strong allergenic reactions in persons exposed to the reaction mixtures was produced. 3,3′-Diindolyl disulfide was found to be allergenic in minute amounts.Keywords
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