83663-37-0Relevant academic research and scientific papers
Bromothiophene Reactions. II. A Novel Rearrangement in the Zinc and Acetic Acid Reduction
Alvares-Insua, A. S.,Conde, S.,Corral, C.
, p. 713 - 716 (2007/10/02)
The elimination of the α-bromine atoms of the bromothienylethanolamine derivatives 2a, b, c, d with zinc and acetic acid unexpectedly involved a migration of the ethanolamine side chain from the 3 to the 2 position in the thiophene ring.Experiments carried out with simpler analogous compounds 3, 4 and 6 seem to indicate that this rearrangement takes place only in those cases in which the carbon atom of the side chain next to the ring supports an oxygen atom capable of being protonated in the reaction medium.A tentative mechanism is proposed to explain the experimental results.
