The reactions of polyhalogenomethanes with aldehydes and with 1,3,5-trinitrobenzene in the presence of tin(II) salts: evidence for the formation of trihalogenomethyl anions

Abstract

The (previously reported) formation of 2,2,2-tribromoethanols by the reaction of aromatic aldehydes with tetrabromomethane in the presence of tin(II) fluoride in dimethyl sulphoxide solution also occurs when tin(II) chloride is used in place of the fluoride. Analogous reactions occur with certain other tetrahalogenomethanes, but not with trihalogenomethanes nor with fluorine-containing tetrahalogenomethanes. When the aldehyde is replaced by 1,3,5-trinitrobenzene, Meisenheimer adducts derived from trihalogenomethyl anions are formed. The trihalogenomethyl anions are thought to be a product of the two-electron reduction of tetrahalogenomethanes by tin(II).