2-Methyl-6,6-bis(trifluoromethyl)cyclohex-3-ene-1-carbaldehyde: Reactivity and Application as a Model for the Preparation of 16,16,16,17,17,17-Hexafluororetinal Analogs
S. Boichut1, C. Boyer2, K. Burger3, A. Haas4, K. Merz5, T Pages6, T. Wallmichrath7
1 Department of Chemistry, Ruhr University of Bochum, D-44780 Bochum (Germany)
2 Department of Chemistry, Ruhr University of Bochum, D-44780 Bochum (Germany)
3 Department of Organic Chemistry, University of Leipzig, D-04103 Leipzig (Germany)
4 Department of Chemistry, Ruhr University of Bochum, D-44780 Bochum (Germany), alois.haas@web.de
5 Department of Chemistry, Ruhr University of Bochum, D-44780 Bochum (Germany)
6 Department of Chemistry, Ruhr University of Bochum, D-44780 Bochum (Germany)
7 Department of Chemistry, Ruhr University of Bochum, D-44780 Bochum (Germany)
Страницы: 23-29
Аннотация
New approaches to 16,16,16,17,17,17-hexafluororetinal and analogs, via 2-methyl-6,6-bis(trifluoromethyl)cyclohexanone and 2-methyl-6,6-bis(trifluoromethyl)cyclohex-1-ene-1-carbaldehyde (7,7,7,8,8,8-hexafluoro-b-cyclocitral) are disclosed. An efficient synthesis for 2-methyl-6,6-bis(trifluoromethyl)-cyclohex-3-ene-1-carbaldehyde, starting from hexafluoroacetone, is described and used for preparing reactive building blocks. The crystal structures of 6, 15 and 23 are provided and the influence of the bis(trifluoromethyl) group on bond lengths and angles is discussed.
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