65369-28-0Relevant academic research and scientific papers
Fries Rearrangement of some 3-Acetoxy- and 3-Propionyloxy-thiophenes
Banks, Malcolm R.
, p. 507 - 514 (2007/10/02)
The Fries rearrangement of ten 3-alkanoyloxythiophenes has been studied in dichloromethane using aluminium chloride as catalyst.An intermolecular component of the mechanism has been demonstrated by the observation of all possible mixed products in approximately equal proportions in a crossover experiment. 3-Alkanoyloxythiophenes were prepared from the corresponding 3-hydroxythiophenes and the rearrangement proceeded generally at ambient temperature to give 3-hydroxy-2-alkanoylthiophenes in good yields.This synthetic route provides a useful alternative to the Friedel-Crafts alkanoylation.The structures of both the acyl and 3-thiophenoxy moieties were found to exert an influence on the rearrangement.Acetyl esters rearranged at a faster rate than propionyl esters.An ester or cyano group in the 4-position did not interfere with the rearrangement whereas an acetyl group prevented it; two ester groups in the tiophene ring also prevent rearrangement occuring yielding 3-hydroxythiophenes in almost quantitative yield.
Aromatization of Dihydrothiophenes. Thiophenesaccharin: A Sweet Surprise
Rossy, Phillip A.,Hoffmann, Werner,Mueller, Norbert
, p. 617 - 620 (2007/10/02)
Sulfuryl chloride has been shown to be highly effective in the dehydrogenation of 3,4-disubstituted-2,5-dihydrothiophenes and 2,3-disubstituted-4,5-dihydrothiophenes, in which the 3,4 and 2,3 substitutents are part of a β-keto carbonyl functionality or it
Thiophene compounds and their manufacture
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, (2008/06/13)
New thiophene compounds and a new process for the manufacture of thiophene compounds by dehydrogenating dihydrothiophene with certain halogen compounds. The products are starting materials for the manufacture of pharmaceuticals, dyes and plant protection agents and, in particular, for the manufacture of additives to foodstuffs, feeds, beverages and pharmaceuticals.
