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5‐Substituted Benzothiophenes: Synthesis, Mechanism, and Kinetic Studies
Author(s) -
Cerminara Iole,
D'Alessio Luciano,
D'Auria Maurizio,
Funicello Maria,
Guarnaccio Ambra
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500285
Subject(s) - acetal , chemistry , computational chemistry , reaction mechanism , mechanism (biology) , kinetic energy , product (mathematics) , organic chemistry , catalysis , philosophy , physics , geometry , mathematics , epistemology , quantum mechanics
The kinetics of the reaction of 4‐methoxythiophenoxyacetaldehyde diethyl acetal, 4‐nitrothiophenoxyacetaldehyde diethyl acetal, and 3‐methoxythiophenoxyacetaldehyde diethyl acetal in polyphosphoric acid has been explained. The kinetic behavior has been explained on the basis of aided simulation and on the basis of density functional theory calculations showing a different pathway for 4‐nitrothiophenoxyacetaldehyde diethyl acetal and for 4‐methoxythiophenoxyacetaldehyde diethyl acetal. In this last case, a very fast competing reaction to the dimerization product was observed.