Journal of the American Chemical Society p. 2520 - 2524 (1984)
Update date:2022-08-11
Topics:
Swartz, James E.
Stenzel, Timothy T.
Electrochemical reduction of benzonitrile in the presence of bromobenzene and tetra-N-butylammonium benzenethiolate in dimethyl sulfoxide (Me2SO) forms diphenyl sulfide (67percent) and benzene (38percent).The reaction consumes 0.37 faraday per mol of bromobenzene, indicating that an SRN1 chain reaction is occuring.Reaction in Me2SO-d6 gives a decreased yield of benzene (17percent), 57percent of which was monodeuterated, which along with coulometric data indicates that a major termination pathway is abstraction of hydrogen atoms from Me2SO by phenyl radicals.Photoinitiated reactions in the presence and absence of tetra-N-butylammonium ions indicate that they are also a significant source of hydrogen atoms in termination.Evidence from reactions of 4-bromotoluene with benzenethiolate ion indicates that fragmentation of the diaryl sulfide radical anion intermediate is an important reaction in these systems.The presence of benzonitrile suppresses that cleavage.
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