Triphenylphosphine dibromide: A useful reagent for conversion of aldoximes into nitriles

9-Anthraldehyde oxime: a synthetic tool for variable applications

“…Darvish and co-workers [39] proposed a facile method for the dehydration of 9-anthraldehyde oxime by using triphenylphosphine dibromide and K 2 CO 3 in acetonitrile at room temperature; the anthracene-9-carbonitrile (36) was obtained in excellent yields (96%, Scheme 19). The same dehydration has been done with H 2 SO 4 /SiO 2 solid support, under microwave irradiation in dry media; the conversion proceeded in short time and allowed for the obtaining of the corresponding nitrile in high yield (85%) [40].…”

“…1,3-Dipolar cycloaddition reactions are one of the most important methods for synthesis of isoxazoline and this cornerstone has been introduced by R. Huisgen in the early 1960s [59]. Recently, Quadrelli and co-workers [60] (40) was obtained in 14% yield [61]. Better yields (68%) can be obtained upon generating the stable nitrile oxide 8a by oxidation of the oxime 2 with NaBrO 2 and tri-n-butyltin chloride and subsequent cycloaddition reaction with methyl acrylate.…”

Efficient formation of nitriles in the vapor-phase catalytic dehydration of aldoximes

“…This is because most of the previous studies were performed in the liquid phase and aldoximes were diluted by a large amount of solvents. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] In the vapor-phase benzaldoxime and 4-methoxybenzaldoxime dehydration over zeolites, organic solvents such as benzene and acetonitrile were also used to dilute the aldoximes. 24,25 In this study, the effect of reaction heat was investigated under solvent-free conditions.…”

“…19,20 Additionally, organic solvents were generally used in the above mentioned reports. [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Microwave-promoted dehydration of aldoximes to nitriles has also been investigated using H 2 SO 4 /SiO 2 , 21 silica gel 22 and zeolites, 23 whereas this process has a limitation of production scale. On the other hand, vapor-phase dehydration of aldoximes to nitriles over solid catalysts has rarely been reported.…”