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Addition of benzyne to thiophene—a DFT study
Author(s) -
Smith William B.
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.851
Subject(s) - aryne , chemistry , thiophene , computational chemistry , activation energy , medicinal chemistry , path (computing) , organic chemistry , computer science , programming language
The literature reports the 2 + 2‐ and 4 + 2‐cycloadditions of benzyne and thiophene and provides several reaction paths accounting for the observed products: 1‐naphthyl and 2‐naphthyl phenyl sulfides. A DFT study of these paths shows that some presumed reaction intermediates are, in fact, not stable entities. A new reaction path adapting a portion of the literature paths but with a lower activation free energy is described. Copyright © 2004 John Wiley & Sons, Ltd.