A RAPID AND FACILE CONVERSION OF PRIMARY AMIDES AND ALDOXIMES TO NITRILES AND KETOXIMES TO AMIDES WITH TRIPHENYLPHOSPHINE ANDN-CHLOROSUCCINIMIDE

A Tungsten–Tin Mixed Hydroxide as an Efficient Heterogeneous Catalyst for Dehydration of Aldoximes to Nitriles

“…These results show that the nature of the observed catalysis is truly heterogeneous. [17] The dehydration hardly proceeded in the absence of catalysts ( 4 , and a physical mixture of WO 3 and Sn(OH) 4 were not effective for the dehydration (Table 1, entries 5-8). According to our experiments, previously reported solid catalysts such as montmorillonite, [12] KF/Al 2 O 3 , [15] and [{RuCl 2 (p-cymene)} 2 ]/C [11] were not effective for dehydration under the present conditions (Table 1, entries 14-16).…”

“…Therefore, efficient catalytic procedures for the dehydration of aldoximes are still in great demand. Oxorhenium(VII) complexes, [5] Ga(OTf) 3 , [6] InCl 3 , [7] TiCl 3 (OTf), [8] and Cu(OAc) 2 [9] have been reported to catalyze the dehydration homogeneously, for example. Although heterogeneous dehydration systems are environmentally and technologically the most desirable procedures, widely usable truly heterogeneous catalysts are unprecedented (see Table 1 and the Supporting Information).…”

“…[2][3][4][5][6][7][8][9][10][11][12][13][14][15] However, selective dehydration to the corresponding nitriles is very difficult, and many reported procedures require the use of reactive reagents in stoichiometric amounts, such as the Burgess reagent, [2] N-chlorosuccinimide/ PPh 3 , [3] and thionyl chloride. [4] Such reagents present a severe drawback for scaled-up and industrial applications.…”

O‐Alkylation of Pyridine Aldo‐ and Ketoximes with Dihalohydrins under Phase‐Transfer Conditions

“…NaOH system in the presence of tetradecylammonium bromide proceeds regiospecifically to afford the corresponding O-halohydrins in good yields. In this study, first O-halohydrin derivatives were converted into glycidyl ether derivatives, and then a new series of amino alcohols were synthesized by the condensation of amines with these glycidyl ethers.Oximes and their derivatives are important intermediates in organic synthesis, especially for protection, alkylation, [1 -4] and regeneration of carbonyl compounds; [5 -10] in the synthesis of hydroxyl amines and primary amines, [11,12] nitrones, [4,13,14] and nitriles; [15 -18] and also in the preparation of pharmaceutical derivatives. [1,2,19 -22] The amino alcohol derivatives obtained from these oximes have properties such as b-adrenergic blocking activity and in vitro b-adreno receptors.…”

Selective Tandem Synthesis of Oximes from Benzylic Alcohols Catalyzed with 2, 3-Dichloro-5, 6-dicyanobenzoquinone

“…Oximes are stable and highly crystalline compounds which may be used as intermediates for the preparation of nitriles via dehydration, 2,3 amides by the Beckmann rearrangement, 4 nitrones, 5 hydroximinoyl chlorides, 6 nitrile oxides, 6 chiral α-sulfinyl oximes, 7 and nitro compounds. 8 Furthermore, oximes are useful selective α-activating groups 9 and also have served for the protection of carbonyl groups.…”