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Synthesis 1999; 1999(4): 644-649
DOI: 10.1055/s-1999-3455
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Organophosphorus Compounds; 141. Phosphorus-Containing Cage Compounds from the Reaction of 7,8-Dichlorocycloocta-1,3,5-triene with tert-Butylphosphaacetylene and Subsequent Chemistry

Oliver Löber* , Uwe Bergsträßer, 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 1999 (online)

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tert-Butylphosphaacetylene (1) reacts at 120 °C with the bicyclic form of cis-7,8-dichlorocycloocta-1,3,5-triene (11) in a Diels-Alder reaction to furnish the tricyclic product 12, whose constitution was confirmed by single crystal structure analysis of the corresponding η 1-pentacarbonyltungsten complex 14. Compound 12 possess a sterically fixed 1,4-diene system and fulfills the structural prerequisite for homo-Diels-Alder reactions, which can be realized with the electron-poor acetylenes 15 as well as phosphaacetylene 1 (→ 16, 20). Furthermore, the polycyclic systems 16 can be oxidized and complexed at the phosphorus atom (→ 18, 19).

phosphaacetylenes - cis-7,8-dichlorocycloocta-1,3,5-triene - [4 + 2] cycloaddition - homo-Diels-Alder reaction - polycyclic cage compounds

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