Unexpected Reactivity of 3-(Phenylethynyl)-1H-indenes towards Nucleophiles: Noncatalytic Addition to Triple Bond with or without Double Bond Migration

P. V. Ivchenko; I. E. Nifant’ev; Yu N. Luzikov; S. G. Mkoyan

doi:10.1055/s-2007-965957

PAPER

Unexpected Reactivity of 3-(Phenylethynyl)-1H-indenes towards Nucleophiles: Noncatalytic Addition to Triple Bond with or without Double Bond Migration

P. V. Ivchenko*^a, I. E. Nifant’ev^a, Yu. N. Luzikov^a, S. G. Mkoyan^b
^a M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, Moscow, 119992, Russian Federation
Fax: +7(495)9394523; e-Mail: inpv@org.chem.msu.ru;
^b Institute of Problem of Chemical Physics of the Russian Academy of Science, 1 Akademika Semenova Prospect, Chernogolovka, Moscow Region, 142432, Russian Federation

Abstract

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Abstract

When studying the chemical properties of (3-phenylethynyl)-1H-indenes, a new reaction was discovered, namely, nucleophilic addition to conjugated enynes accompanied in some cases by migration. The reaction takes place under mild conditions and is not catalyzed by transition metal complexes. A putative reaction mechanism via an allene intermediate is discussed.

Key words

alkynes - allenes - enynes - nucleophilic additions - rearrangements

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References

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