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Stereochemical Evidence Supporting the Intermediate‐Mechanism of Dihalocarbene Addition
Author(s) -
Dehmlow Eckehard V.,
Kramer Roland
Publication year - 1984
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.198407061
Subject(s) - cyclooctene , dichlorocarbene , adduct , chemistry , mechanism (biology) , stereochemistry , reactive intermediate , medicinal chemistry , catalysis , organic chemistry , philosophy , epistemology
That the addition of dibromocarbene to alkenes proceeds via an intermediate (IN) follows from observations on trans ‐cyclooctene 1 . The less reactive dichlorocarbene furnishes the expected trans ‐adduct 2 ; dibromocarbene, however, does not add stereospecifically, and isomerizes the unreacted 1 to cis ‐cyclooctene, cis ‐ 1 . This affords evidence of involvement of an intermediate—most likely a CT complex.
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