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Synthesis 2020; 52(22): 3397-3405
DOI: 10.1055/s-0040-1707349
DOI: 10.1055/s-0040-1707349
special topic
Controlling the All-trans Stereochemistry in Liquid Crystalline 4,4′-Dialkyl-[1,1′-bicyclohexyl] Compounds
Weitere Informationen
Publikationsverlauf
Received: 12. Mai 2020
Accepted after revision: 24. Juni 2020
Publikationsdatum:
05. August 2020 (online)
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.
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