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Apparently Nonstereospecific Dihalocarbene Addition—an Explanation
Author(s) -
Dehmlow Eckehard V.,
Stiehm Thomas
Publication year - 1987
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.198703291
Subject(s) - carbene , isomerization , chemistry , catalysis , nucleophile , medicinal chemistry , nucleophilic addition , photochemistry , organic chemistry
Reversible formation of :CX 2 from :CX 3 ⊖under phase‐transfer‐catalysis conditions could explain the nonstereospecific carbene addition observed for 1 . Reversible nucleophilic addition of :CX 3 ⊖results in the isomerization of 1 to 2 ; the subsequent carbene addition to 1 and 2 to give 3 and 4 , respectively, occurs stereospecifically, as expected (X = C1, Br).