Download PDF
Synlett 1993; 1993(5): 344-347
DOI: 10.1055/s-1993-22449
letter
© 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.

Multiple Dissolving-Metal Reduction of Centropolyindans: Synthesis of a Hexakis(cyclohexano)centrohexaquinacene

Ralf Eckrich* , Dietmar Kuck
  • *Fakultät für Chemie der Universität Bielefeld, Universitätsstrasse 25, D-4800 Bielefeld 1, Germany
Further Information

Publication History

Publication Date:
19 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Four prototype centropolyindans 1, 3, 7, and 10 were subjected to reduction with Li/NH3 and Li/NH2Me. While Birch reduction of 1, 3, and 7 gives medium to good yields of the corresponding two-, three-, and sixfold 1,4-cyclohexadienes 2, 4, and 8, respectively, centrohexaindan 10 does not react at all. With Li in NH2Me, however, 10 is converted to the corresponding hexaene, the title compound 12. Similarly, Benkeser reductions of 1 and 7 give the corresponding triquinacene 6 and the [3.3.3]propellatriene 9. Preliminary epoxidation and hydrogenation experiments of some polycyclic olefins are presented.

      >