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Stereochemistry of the CS Bond Cleavage in 1‐Phenylethyl Phenyl Sulfide Radical Cation: Evidence for a Unimolecular Pathway
Author(s) -
Baciocchi Enrico,
Fasella Elisabetta,
Lanzalunga Osvaldo,
Mattioli Mario
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199310711
Subject(s) - chemistry , bond cleavage , radical ion , sulfide , cleavage (geology) , reaction mechanism , stereochemistry , medicinal chemistry , computational chemistry , photochemistry , catalysis , organic chemistry , ion , geotechnical engineering , engineering , fracture (geology)
Is the bond‐cleavage mechanism uni‐ or bimolecular in the reaction (a)? The search for the answer involved the use of enantiomerically pure ( R )‐(+)‐ 1 , reaction conditions with or without base, and detailed product analyses. The experimental results are consistent with a unimolecular pathway, which initially leads to a contact radical cation pair and then to a solvent‐separated radical cation pair.