Abstract
AbstractOn treatment of 2‐bromothiophene, 2,3‐, 2,4‐, and 2,5‐dibromothiophene with potassium amide in liquid ammonia at − 75°, a bromine migration of position α to position β of the thiophene ring takes place. On treatment of the above mentioned compounds with potassium amide in liquid ammonia at − 33°, besides α to β bromine rearrangement, amination to 3‐aminothiophene was observed.The mechanism of the transbromination is assumed to be an intermolecular process, involving dibromo‐ and tribromo‐thiophenes. The formation of 3‐aminothiophene does not occur via a didehydro intermediate, but it is the result of amination of a polybromothiophene, yielding an amino‐bromothiophene, which is debrominated by reaction with amide ion or a thiophene anion.
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