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Synthesis 2002(14): 2129-2137
DOI: 10.1055/s-2002-34390
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Liquid Crystalline Properties of 5-Alkyl-1,4-dioxane-2-carboxylic­ Esters

Manfred Braun*a, Birgit Spiekera, Antje Hahna, Volkmar Villb
a Institut für Organische Chemie und Makromolekulare Chemie, Universität Düsseldorf, 40225 Düsseldorf, Germany
Fax: +49(211)8115079; e-Mail: braunm@uni-duesseldorf.de;
b Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146, Germany
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Publikationsverlauf

Received 14 June 2002
Publikationsdatum:
26. September 2002 (online)

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Abstract

The first route to 5-alkyl substituted and purely trans-configurated 1,4-dioxanecarboxylic acids 3 is described. The mesogenic properties of the esters 17 and 20, which are derived from the acids 3 and esters 19 (prepared from the hemiacetal 8a), are studied and compared. An enantioselective route to 1,4-dioxanecarboxylic acid 3a is explained, and takes advantage of the stereoselective addition of the bromolithioalkene 11b to heptanal.

Key words

heterocycles - esters - stereoselective synthesis - liquid crystals - ring closure

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15

The corresponding 1,3-dioxanecarboxylic ester forms only a nematic phase: Vill, V. unpublished results, Univ. Hamburg 1998.