2‐Ethylhexanonitrile

Abstract

2‐Ethylhexanonitrile product: 2‐Ethylhexanonitrile reactant: 286 g. (2 moles) of 2‐ethylhexanamide product: palmitonitrile

Hydrosilanes Are Not Always Reducing Agents for Carbonyl Compounds but Can Also Induce Dehydration: A Ruthenium‐Catalyzed Conversion of Primary Amides to Nitriles

“…However, an intramolecular esterification reported by Mukaiyama is the only precedence for an organohydrosilanes behaving as dehydrating reagents, in which a substrate containing two acidic protons and an oxygen atom reacts with a hydrosilane with the aid of a rhodium catalyst and a strong Lewis acid, which leads to the elimination of a siloxane. Synthesis of nitriles by dehydration of primary amides conventionally requires strongly acidic and vigorously reactive reagents12 such as phosphorus pentoxide,12c titanium tetrachloride,12d or thionyl chloride 12e. Although several dehydrating reagents that can be used under milder conditions have been devised recently,13 only a few reactions occur under neutral conditions 14.…”

Dehydration of Chiral α-Amides to Chiral α-Nitriles Under the Appel Reaction Conditions

“…The most common way to synthesize nitriles is by dehydration of primary amides. This involves the use of acidic dehydrating reagents viz., P 2 O 5 (Reisener and Horning 1963), POCl 3 (Rickborn and Jensen 1962), SOCl 2 (Krynitsky and Carhart 1963), and TiCl 4 (Lehnert 1971). In an attempt, sophisticated reagents, such as the combination of ethyl dichlorophosphate and diazabicyclo[5.4.0]undec-7ene (DBU), were also used for the dehydration of amides (Kuo et al 2007).…”

Highly-Efficient Conversion of Primary Amides to Nitriles Using Indium(III) Triflate as the Catalyst

“…Another practical method to form nitriles is the dehydration of primary amides. There are a number of reports concerning the dehydration of primary amides conducted with stoichiometric amounts of acidic reagents such as P 2 O 5 [7], [8], POCl 3 [9], SOCl 2 [10]- [12], aryl chlorothionoformate [13], trifluoroacetic anhydride [14], and trichloroisocyanuric acid [15]. However, in many cases, implementation with these acidic reagents may not be appropriate, particularly for compounds that possess acid sensitive substrates.…”