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Highly Substituted Spiro[4.4]nonatrienes from a β ‐Amino‐Substituted α , β ‐Unsaturated Fischer Carbene Complex and Three Molecules of an Arylalkyne
Author(s) -
Schirmer Heiko,
Duetsch Michael,
Stein Frank,
Labahn Thomas,
Knieriem Burkhard,
de Meijere Armin
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990503)38:9<1285::aid-anie1285>3.0.co;2-n
Subject(s) - carbene , alkyne , trimethylsilyl , chemistry , molecule , transition metal carbene complex , stereochemistry , medicinal chemistry , organic chemistry , catalysis
A novel mode of reaction towards arylethynes is shown by the β ‐trimethylsilyl‐substituted α , β ‐unsaturated Fischer carbene complexes 1 . A mixture of the isomeric, highly substituted spiro[4.4]nonatrienes 2 and 3 is formed by the formal insertion of three alkyne molecules and subsequent cyclization (see scheme). Such selective triple insertions of alkynes into ethenylcarbene complexes have not been previously observed.