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Abstract The carbene adducts 3a-c (R1 = Me, Et, iso-Pr; R2 = Me) are formed from the 2,3-dihydro-imidazol-2-ylidenes 1a-c and 1,2-dichloroethane as air-sensitive solids in good yields. The compounds exhibit a reactive Cl-Cl bond. Benzene is chlorinated by 3a,b to give chlorobenzene and the imidazolium salts 10a,b under mild conditions. 3c acts as a chloride donor to give with AICI3 and SO2 the 2-chloroimidazolium salts 12c and 13c (X = AlCl4, SO2Cl). On hydrolysis, the less reactive hydrate salt 14c is formed from 3c. The X-ray structures of 10a and 14c are reported.
Received: 1998-2-23
Published Online: 2014-6-2
Published in Print: 1998-7-1
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