Download PDF
Synthesis 1999; 1999(4): 644-649
DOI: 10.1055/s-1999-3455
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

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