Controlling the All-trans Stereochemistry in Liquid Crystalline 4,4′-Dialkyl-[1,1′-bicyclohexyl] Compounds

Andreas Wächtler; Matthias Bremer; David Maillard; Thomas Mohr

doi:10.1055/s-0040-1707349

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(22): 3397-3405
DOI: 10.1055/s-0040-1707349

special topic

Controlling the All-trans Stereochemistry in Liquid Crystalline 4,4′-Dialkyl-[1,1′-bicyclohexyl] Compounds

Authors

Andreas Wächtler∗

^aAndreas Wächtler, Consultant, Am Hopfengarten 16, 64295 Darmstadt, Germany eMail: andreas.waechtler@external.merckgroup.com eMail: andreas.waechtler@t-online.de
Matthias Bremer ∗

^bMerck KGaA, Frankfurterstr. 250, 64293 Darmstadt, Germany eMail: matthias.bremer@merckgroup.com
David Maillard

^bMerck KGaA, Frankfurterstr. 250, 64293 Darmstadt, Germany eMail: matthias.bremer@merckgroup.com
Thomas Mohr

^bMerck KGaA, Frankfurterstr. 250, 64293 Darmstadt, Germany eMail: matthias.bremer@merckgroup.com

Abstract

Alle Artikel dieser Rubrik

Published as part of the Special Topic Synthesis in Industry

Dedicated to the memory of Professor Dr. Dr. h. c. Michael Hanack (1931–2019). A.W. thanks him for 40 years of continuous encouragement.

Abstract

A good part of today’s liquid crystals (LCs) for display applications are derived from the Darzens–Nenitzescu reaction which, in a one-pot-process, yields 1,4-trans-acylphenylcyclohexanes from acid chlorides, benzene, and cyclohexene. A mechanism for this process is proposed based on quantum-chemical computations. The products of this reaction can be further elaborated to all-trans-4,4′-disubstituted-[1,1′-bicyclohexane] compounds, essential components in almost all fast switching LC-mixtures. An equilibration process involving carbocations is used to control the diastereomer distribution.

Key words

liquid crystals - Darzens–Nenitzescu reaction - carbocations - cation-induced configurational isomerization (CICI)

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Referenzen

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