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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

✍ Scribed by Heiko Schirmer; Michael Duetsch; Frank Stein; Thomas Labahn; Burkhard Knieriem; Armin de Meijere

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 95 KB
Volume: 38
Category: Article
ISSN: 0044-8249
DOI: 10.1002/(sici)1521-3773(19990503)38:9<1285::aid-anie1285>3.0.co;2-n

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✦ Synopsis

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.

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