- Different outcomes in the reactions of WCl6 with carboxylic acids
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Abstract The reactions of WCl6 with a selection of carboxylic acids were investigated by using dichloromethane as reaction medium. The addition of pyridine-3-carboxylic acid (niacin) to WCl6 gave [C5H4NHC(O)Cl][WOCl5], 1, in 75% yield via selective Cl/O interchange. WCl6 reacted with RCO2H (R = CH3, CBr3, CHCl2) in 1:2 ratio resulting in the formation of HCl and the respective acyl chlorides, RC(O)Cl. WOCl4(κ1-CH3CO2H), 2, was isolated from WCl6/CH3CO2H in 41% yield. The 1:2 reaction of WCl6 with CCl3CO2H proceeded with HCl release affording a mixture of WCl5(O2CCCl3), 3, and WCl4(O2CCCl3)2, 4. Compound 3 was isolated from WCl6/CCl3CO2H (1:1 ratio) in 60% yield. All the metal products were characterized by analytical and spectroscopic techniques. The crystal structure of 1 was ascertained by X-ray diffractometry. DFT calculations were carried out in order to shed light into structural, mechanistic and thermodynamic features.
- Bortoluzzi, Marco,Guarra, Federica,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano
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- Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of [6]Hexahelicene-7-carboxylic acid
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A convergent synthesis of racemic [6]hexahelicene-7-carboxylic acid by cross-coupling of a bicyclic and a tricyclic component is described. A metal-catalyzed ring-closure is also a fundamental component of the synthetic approach. Scanning tunneling microscopy (STM) measurements of the racemate self-assembled on Au(111) at liquid–solid interface revealed the formation of ordered racemic 2D crystals.
- van der Meijden, Maarten W.,Balandina, Tatyana,Ivasenko, Oleksandr,De Feyter, Steven,Wurst, Klaus,Kellogg, Richard M.
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p. 14633 - 14639
(2016/10/03)
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