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Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols
Institute of Chemical Process Fundamentals of AS CR, v.v.i., Rozvojová 135, 165 02 Prague 6, Czech Republic
Department of Chemistry, Faculty of Science, Purkynje University Ústí nad Labem, České mládeže 8, 400 96 Ústí nad Labem, Czech Republic
* Author to whom correspondence should be addressed.
Received: 23 March 2011; in revised form: 4 May 2011 / Accepted: 11 May 2011 / Published: 17 May 2011
Abstract: (Perfluoroalkyl) tetramethylcyclopentenols (alkyl = n-butyl, n-hexyl, n-octyl) were dehydrated to a complex mixture of endo, endo-(perfluoroalkyl) tetramethyl-cyclopentadienes and their endo-, exo-isomers. It was found in preliminary screening experiments that the best reagent for this transformation, giving an 89% yield of isomeric product mixture, was P2O5 in benzene at 80-90 °C. Products were characterized on the basis of their mass spectra and retention time information, and some peaks in the mass spectra were identified from their molecular fragments. Structures were assigned to the three most abundant products of (perfluorohexyl)tetramethylcyclopentenol dehydration. Formal dehydration kinetics showed a second order reaction in benzene but zeroth order with induction period in chlorobenzene, suggesting mass transfer limitations in the more polar chlorobenzene. Some of the products were formed by consecutive isomerization of the others, as shown by the kinetic analysis.
Keywords: dehydration; fluorous cyclopentadienes; cyclopentenols
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Čermák, J.; Nguyen Thi, T.H.; Včelák, J.; Krupková, A. Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols. Molecules 2011, 16, 4031-4044.
Čermák J, Nguyen Thi TH, Včelák J, Krupková A. Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols. Molecules. 2011; 16(5):4031-4044.
Čermák, Jan; Nguyen Thi, Thu Huong; Včelák, Jaroslav; Krupková, Alena. 2011. "Dehydration of (Perfluoroalkyl)tetramethylcyclopentenols." Molecules 16, no. 5: 4031-4044.