Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Imidazole Derivatives, XIXPart XVIII: Ref. . - Coordination or reduction? On the Reaction of 1,3-Diisopropyl-4,5-dimethylimidazol-2-ylidene with Sulfur Halides and Sulfur Oxygen Halides Herrn Professor Max Herberhold zum 60. Geburtstag gewidmet.The reaction of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (4, Im) with sulfur halides and sulfur oxygen halides may be described as a coordination (1) or reduction (2) process in respect to the sulfur centre. With SCl2 and SOCl2 the hypervalent sulfur compounds Im · SCl2 (5) and Im · S(O)Cl2 (13) are obtained. The SF2 adduct Im · SF2 (11) is formed on treatment of 5 with AgF. 13 is alkylated by methyl iodide to give the Im · S(Me)OCl2 cation (15). Surprisingly, reduction of the sulfur centre (2) occurs on treatment of 4 with SF4 to form the ImF+SF3- salt 18 containing the new SF3 anion. As expected, the same type of reaction occurs with the sulfuryl halides SO2ClF and SO2F2 to give the fluorosulfites ImCl+-SO2F- (21) and ImF+SO2F- (23). The X-ray structures of 5, 13 and 23 are reported.
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