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Thermolysis of trifluoromethyl-containing vinyldiazocarbonyl compounds and X-ray crystal structure analysis of unexpected reaction products


Nikolaev, Valerij A; Supurgibekov, Murat B; Haiges, Ralf; Linden, Anthony; Prakash, G K Surya (2013). Thermolysis of trifluoromethyl-containing vinyldiazocarbonyl compounds and X-ray crystal structure analysis of unexpected reaction products. Journal of Fluorine Chemistry, 156:322-326.

Abstract

Two unusual compounds, 1,3a,6,6a-tetrahydro-3a,6a-bis(trifluoromethyl)-cyclopenta[c]pyrazol-3,4,5,6-tetracarboxylic acid tetramethyl ester (C16H14N2O8F6) (3) and 2-acetyl-5,7-bis(trifluoromethyl)-4-methyl-3-methoxy-2,4,6-cycloheptatrienecarboxylic acid methyl ester (C14H11F6O3) (4), were obtained from thermolysis of 3-trifluoromethyl-substituted vinyldiazocarbonyl compounds. The crystal structures of the products were determined as part of a larger comparison study on the thermal and Rh(II)-catalyzed reactions of F- and H-vinyldiazocarbonyl compounds. The resulting structures provide the first crystallographic characterization of bis(trifluoromethyl)substituted compounds of this kind. The pure compounds with all-carbon (4) and half-heterocyclic (3) skeletons are composed of a
seven- and two-annulated five-membered rings in folded butterfly and envelope conformations, respectively.

Abstract

Two unusual compounds, 1,3a,6,6a-tetrahydro-3a,6a-bis(trifluoromethyl)-cyclopenta[c]pyrazol-3,4,5,6-tetracarboxylic acid tetramethyl ester (C16H14N2O8F6) (3) and 2-acetyl-5,7-bis(trifluoromethyl)-4-methyl-3-methoxy-2,4,6-cycloheptatrienecarboxylic acid methyl ester (C14H11F6O3) (4), were obtained from thermolysis of 3-trifluoromethyl-substituted vinyldiazocarbonyl compounds. The crystal structures of the products were determined as part of a larger comparison study on the thermal and Rh(II)-catalyzed reactions of F- and H-vinyldiazocarbonyl compounds. The resulting structures provide the first crystallographic characterization of bis(trifluoromethyl)substituted compounds of this kind. The pure compounds with all-carbon (4) and half-heterocyclic (3) skeletons are composed of a
seven- and two-annulated five-membered rings in folded butterfly and envelope conformations, respectively.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Vinyldiazo compounds Pyrazoles Fluoroalkyl-containing compounds Cycloheptatrienes Diazabicyclooctadienes
Language:English
Date:2013
Deposited On:16 Dec 2013 13:48
Last Modified:05 Apr 2016 17:15
Publisher:Elsevier
ISSN:0022-1139
Funders:Loker Hydrocarbon Research Institute
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2013.07.019

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