Diethylaluminium cyanide has not been examined by X-ray crystallography, although other diorganoaluminium cyanides have been. Diorganylaluminium cyanides have the general formula (R2AlCN)n, and they exist as cyclic trimers (n = 3) or tetramers (n = 4). In these oligomers, one finds AlCN---Al linkages. One compound similar to diethylaluminium cyanide is bis[di(trimethylsilyl)methyl]aluminium cyanide, ((Me3Si)2CH)2AlCN, which has been shown crystallographically to exist as a trimer with the following structure:[4]
Bis(tert-butyl)aluminium cyanide, tBu2AlCN exists as a tetramer in the crystalline phase:[7][8]
Usesedit
Diethylaluminium cyanide is used for the stoichiometric hydrocyanation of α,β-unsaturated ketones. The reaction is influenced by the basicity of the solvent. This effect arises from the Lewis acidic qualities of the reagent.[9] The purpose of this reaction is to generate alkylnitriles, which are precursors to amines, amides, carboxylic acids esters and aldehydes.
Referencesedit
^ abc"MSDS - 276863". Sigma-Aldrich. Retrieved December 9, 2012.
^Nagata, W (1988). "Diethylaluminum cyanide". Organic Syntheses. VI: 307. doi:10.15227/orgsyn.052.0090.
^Nagata, W. (1966). "Alkylaluminum cyanides as potent reagents for hydrocyanation". Tetrahedron Lett.7 (18): 1913–1918. doi:10.1016/S0040-4039(00)76271-X.
^ abUhl, Werner; Schütz, Uwe; Hiller, Wolfgang; Heckel, Maximilian (1995). "Synthese und Kristallstruktur des trimeren [(Me3Si)2CH]2Al—CN". Z. anorg. allg. Chem.621 (5): 823–828. doi:10.1002/zaac.19956210521.
^Wade, K.; Wyatt, B. K. (1969). "Reactions of organoaluminium compounds with cyanides. Part III. Reactions of trimethylaluminium, triethylaluminium, dimethylaluminium hydride, and diethylaluminium hydride with dimethylcyanamide". J. Chem. Soc.: 1121–1124. doi:10.1039/J19690001121.
^Coates, G. E.; Mukherjee, R. N. (1963). "35. Dimethylaluminium cyanide and its gallium, indium, and thallium analogues; beryllium and methylberyllium cyanide". J. Chem. Soc.: 229–232. doi:10.1039/JR9630000229.
^Uhl, W.; Matar, M. (2004). "Hydroalumination of nitriles and isonitriles" (PDF). Z. Naturforsch. B. 59 (11–12): 1214–1222. doi:10.1515/znb-2004-11-1239. S2CID 99001626.
^Uhl, W.; Schütz, U.; Hiller, W.; Heckel, M. (2005). "Synthese und Kristallstruktur des trimeren [(Me3Si)2CH]2Al—CN" (PDF). Z. Naturforsch. B. 60 (2): 155–163.
^Nagata, W.; Yoshioka, M. (1988). "Diethylaluminum cyanide". Organic Syntheses; Collected Volumes, vol. 6, p. 436.
External linksedit
Media related to Diethylaluminium cyanide at Wikimedia Commons
April 11, 2024
diethylaluminium, cyanide, nagata, reagent, organoaluminium, compound, with, formula, c2h5, 2alcn, this, colorless, compound, usually, handled, solution, toluene, reagent, hydrocyanation, unsaturated, ketones, namesiupac, name, diethylalumanylformonitrileother. Diethylaluminium cyanide Nagata s reagent 2 is the organoaluminium compound with formula C2H5 2AlCN n This colorless compound is usually handled as a solution in toluene It is a reagent for the hydrocyanation of a b unsaturated ketones 1 3 4 5 6 Diethylaluminium cyanide NamesIUPAC name diethylalumanylformonitrileOther names Cyanodiethyl aluminium Cyano kC diethyl aluminium Cyano C diethyl aluminiumCyanodiethyl 7CI 8CI aluminiumCyanodiethylallaneCyanodiethylaluminiumDiethylaluminium CyanideIdentifiersCAS Number 5804 85 3 YECHA InfoCard 100 024 873PubChem CID 16683962PropertiesChemical formula CH3CH2 2AlCNMolar mass 111 124 g mol 1Appearance Dark brown clear liquid 1 0 mol L in toluene 1 Density 0 864 g cm3 at 25 C liquid Boiling point 162 C 324 F 435 K at 0 02 mmHgSolubility in water Reacts with waterSolubility Benzene Toluene diisopropyl etherHazardsFlash point 7 C 45 F 280 K closed cup 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis 2 Structure 3 Uses 4 References 5 External linksSynthesis editDiethylaluminium cyanide was originally generated by treatment of triethylaluminium with a slight excess of hydrogen cyanide The product is typically stored in ampoules because it is highly toxic It dissolves in toluene benzene hexane and isopropyl ether It undergoes hydrolysis readily and is not compatible with protic solvents n Et3Al n HCN Et2AlCN n n EtHStructure editDiethylaluminium cyanide has not been examined by X ray crystallography although other diorganoaluminium cyanides have been Diorganylaluminium cyanides have the general formula R2AlCN n and they exist as cyclic trimers n 3 or tetramers n 4 In these oligomers one finds AlCN Al linkages One compound similar to diethylaluminium cyanide is bis di trimethylsilyl methyl aluminium cyanide Me3Si 2CH 2AlCN which has been shown crystallographically to exist as a trimer with the following structure 4 nbsp Bis tert butyl aluminium cyanide tBu2AlCN exists as a tetramer in the crystalline phase 7 8 nbsp Uses editDiethylaluminium cyanide is used for the stoichiometric hydrocyanation of a b unsaturated ketones The reaction is influenced by the basicity of the solvent This effect arises from the Lewis acidic qualities of the reagent 9 The purpose of this reaction is to generate alkylnitriles which are precursors to amines amides carboxylic acids esters and aldehydes nbsp References edit a b c MSDS 276863 Sigma Aldrich Retrieved December 9 2012 Nagata W 1988 Diethylaluminum cyanide Organic Syntheses VI 307 doi 10 15227 orgsyn 052 0090 Nagata W 1966 Alkylaluminum cyanides as potent reagents for hydrocyanation Tetrahedron Lett 7 18 1913 1918 doi 10 1016 S0040 4039 00 76271 X a b Uhl Werner Schutz Uwe Hiller Wolfgang Heckel Maximilian 1995 Synthese und Kristallstruktur des trimeren Me3Si 2CH 2Al CN Z anorg allg Chem 621 5 823 828 doi 10 1002 zaac 19956210521 Wade K Wyatt B K 1969 Reactions of organoaluminium compounds with cyanides Part III Reactions of trimethylaluminium triethylaluminium dimethylaluminium hydride and diethylaluminium hydride with dimethylcyanamide J Chem Soc 1121 1124 doi 10 1039 J19690001121 Coates G E Mukherjee R N 1963 35 Dimethylaluminium cyanide and its gallium indium and thallium analogues beryllium and methylberyllium cyanide J Chem Soc 229 232 doi 10 1039 JR9630000229 Uhl W Matar M 2004 Hydroalumination of nitriles and isonitriles PDF Z Naturforsch B 59 11 12 1214 1222 doi 10 1515 znb 2004 11 1239 S2CID 99001626 Uhl W Schutz U Hiller W Heckel M 2005 Synthese und Kristallstruktur des trimeren Me3Si 2CH 2Al CN PDF Z Naturforsch B 60 2 155 163 Nagata W Yoshioka M 1988 Diethylaluminum cyanide Organic Syntheses Collected Volumes vol 6 p 436 External links edit nbsp Media related to Diethylaluminium cyanide at Wikimedia Commons Retrieved from https en wikipedia org w index php title Diethylaluminium cyanide amp oldid 1168687216, wikipedia, wiki, book, books, library,
