Tetrabutylammonium iodotetrachloride

The same 8-chloroadenosine (5) is also obtained with tetrabutylammonium iodotetrachloride (TBAIClJ or with tert-butyl hypochlorite (r-BuOCl) in dimethylformamide. Analogous chlorination of -methyladenosine, to give 6, and A. A -dimethyladenosine is also possible with the latter reagent. ... 

Buckles, R. E. Knaack, D. F. J. Org. Chem. 1960, 25, 20 reported that tetrabutylammonium iodotetrachloride gives stereospecific anti addition of chlorine to stilbene and other compounds. The stereospecificity of the reaction was attributed to an unspecified role for the iodotetrachloride or iododichloride ions present in the reaction mixture. 

Tetrabutylammonium iodotetrachloride as ehlorinating agent Stereospecific frans-addition to carbon-carbon double bonds... 

Tetrabutylammonium iodotetrachloride does not appear to be as reactive as molecular chlorine, but the reactions can be controlled more easily.—E A mixture of equimolar amounts of cis-stilbene and tetrabutylammonium iodotetrachloride in ethylene chloride allowed to stand 3 days in the dark -> dl-a,a -dichlorodibenzyl. Y 50%. F. e. s., also replacement of hydrogen by chlorine, s. R. E. Buckles and D. F. Knaack, J. Org. Ghem. 25, 20 (1960). 

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