A novel and simple synthetic route to perfluoroalkylacetaldehydes using commercially available alkali halides and metal oxides

Preparation and Reactions of Aliphatic 2‐Pentafluorosulfanyl Aldehydes

“…Alternatively, direct hydrolysis of 8 by using a mixture of hydrochloric acid and glacial acetic acid is efficient 12. Attempts to use milder conditions with lithium halide or metal oxide salts were not effective 14. The lower yield of 2‐pentafluorosulfanylpentanal 9a (<30 %) was attributed to mechanical losses as a result of the volatility of the compound.…”

The Stability/Reactivity Effects of Trifluoromethyl and Perfluoroalkyl Chains in a Masked 1,3-Dicarbonyl Derivative: The Case of 1-Acetoxy-1-iodo-2-(perfluoroalkyl)ethanes

“…18 In view of the satisfying results obtained with alkali metals, it was envisaged that metal oxides could also react in a similar way, in which nucleophilic-electrophilic interactions between the metal and the iodine atom of the gemiodoacetylated compounds 9 are expected to occur. 17 Conversion was found to be more effective when the oxides were added neat to 9 (Table 3), that is, in the absence of water or any other solvent, particularly in the case of copper oxide, titanium dioxide and zirconium dioxide, the latter giving the best yields. 17 The practical benefits of the reactions described herein include facile preparative-scale applications and low cost of reagents employed.…”

“…17 Conversion was found to be more effective when the oxides were added neat to 9 (Table 3), that is, in the absence of water or any other solvent, particularly in the case of copper oxide, titanium dioxide and zirconium dioxide, the latter giving the best yields. 17 The practical benefits of the reactions described herein include facile preparative-scale applications and low cost of reagents employed. Moreover, these 2-(perfluoroalkyl)ethanals 13 could serve for studying the biodegradation of polyfluorinated compounds, such as certain perfluorinated surfactants.…”

“…13 Furthermore, a very interesting approach involves the reaction of 1-acetoxy-1-iodo-2-(perfluoroalkyl)ethanes 9 with various alkali halides or metal oxides. 17 A six-center intermediate between the gem-iodoacetate and these compounds allows the formation of the corresponding aldehydes 13 by a concerted mechanism (Scheme 10).…”