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Synthesis 2000; 2000(4): 529-536
DOI: 10.1055/s-2000-6380
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Organophosphorus Compounds, Part 153; New Phosphorus-Carbon Cage Compounds by Diels - Alder and Homo Diels - Alder Reactions of 1,3,5-Triphosphabenzenes with Alkynes

Christoph Peters* , Stefanie Stutzmann, Hendrik Disteldorf, Stefan Werner, Uwe Bergsträßer, Carl Krüger, Paul Binger, Manfred Regitz
  • *Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-67663 Kaiserslautern, Germany; Fax +49 (6 31) 2 05 39 21; E-mail: regitz@rhrk.uni-kl.de
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Publication Date:
31 December 2000 (online)

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Eleven new phosphorus-carbon cage compounds 3a-d, 5a-e, 7, and 8 have been synthesized in mostly excellent yields by reactions of the 1,3,5-triphosphabenzenes 1 with acetylene, several monosubstituted acetylenes, and cyclooctyne. While most of the alkynes react with the heterobenzenes 1 in a sequence of Diels - Alder and homo Diels - Alder reactions to furnish the cage-compounds 3a-d, 5a-e, and 7 with the same tetracyclic phosphorus-carbon skeleton, the reaction with tert-butylacetylene leads to the formation of the unexpected polycylic compound 8 by way of an as yet unknown reaction mechanism. The structure of the tetracyclic product 7 as well as that of the cage compound 8 has been confirmed by X-ray crystallographic analyses.

phosphorus-carbon cage compounds - 1,3,5-triphosphabenzenes - Diels - Alder reaction - homo Diels - Alder reaction - cycloadditions - heterocycles