IBA anion (1  ), believed as a resonance hybrid of closed-ring (1A  ) and open-ring structures (1B  ) in solid state, is benzylated by benzyl bromide in CDCl3 to form 1-(benzyloxy)-1,2-benziodoxol-3(1H)-one (2  , major) and benzyl 2-iodobenzoate (4  , minor), indicating that 1A  and 1B  co-exist in solution. Formation of 4  presumably goes through benzyl  2-iodosylbenzoate (3  ), which is rapidly converted to 4  in the presence of bromide. Competitive benzylation experiment showed that 1A  is a slightly better nucleophile than 5-methyl-2-iodobenzoate.

Reaction of IBA anion with benzyl bromide: Evidence for the co-existence of open-ring and closed-ring structures in solution

244th National Meeting (2012)

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