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Synthesis 1999; 1999(1): 117-120
DOI: 10.1055/s-1999-3689
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Synthesis of Rodlike Dispiro Hydrocarbon Skeletons for New Liquid Crystal Compounds

Nina Feuerbacher* , Fritz Vögtle, Jens Windscheidt, Eike Poetsch, Martin Nieger
  • *Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany; Tel. +49(2 28)7 33 49 56; Fax +49(2 28)73 56 62 E-mail: voegtle@uni-bonn.de
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Publication Date:
31 December 1999 (online)

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A simple synthesis of the dispiro[5.2.5.2]hexadecane skeleton was developed. Starting from the cyclohexanedicarbaldehyde 6 the dispirane was prepared in one step. The synthesised dispirodiketone 4 is a key compound for the preparation of a number of new liquid crystalline compounds, as its linear molecular shape is proved by an x-ray structural analysis of the corresponding diketal 10. Additionally the synthesis of the first dispirane 4 with a [5.2.3.2]-linkage is described.

Cyclobutane - Cyclohexane - Ketals - Liquid crystals - Spiro compounds