Oximes oxime

Interestingly, most of the reactions reported with imines and related products such as oximes, oxime ethers, hydrazones and nitrones can be run in aqueous media [103]. 

DIOXAZOLONES, FURAZAN N-OXIDES HYDROXYLAMINIUM SALTS, ISOXAZOLES, 2H-1,2,4-OXADIAZOLO[2,3-a]PYRIDINE-2-TfflONES OXIMES, OXIME CARBAMATES... 

C. Hydroxylamines through Reduction of Oximes, Oxime Ethers... 

HYDROXYLAMINES THROUGH ADDITION TO THE C=N DOUBLE BOND OF OXIMES, OXIME ETHERS AND NITRONES. 139... 

B. Free Radical Additions to Oximes, Oxime Ethers and Nitrones. 142... 

Hydrolysis of nitrones, oximes and hydroxamic acids is frequently used as a final step in the preparation of substituted hydroxylamines. Although hydrolysis is the most commonly utilized method for oximes, oxime ethers and nitrones, formation of sensitive hydroxylamines can also be achieved under milder reaction conditions by treatment of... 

Complex hydrides are reagents of choice for reduction of oximes, oxime ethers and nitrones. Hydrogenation is rarely used for reduction of these compounds although several examples are known. Other methods, especially reduction with silanes in the presence of acid, can also be useful for providing alternative stereochemical outcomes. 

Synthesis of heterocycles from amino amide oximes has been described. Recently we have reviewed the synthesis of oximes, oxime 0-ethers and esters, and also the synthesis of heterocycles from oximes covering the literature data published in 1990-1999 . 

Further evidence for the above chemical shift rule was collected subsequently for systems such as oximes, oxime hydrochlorides, hydrazones, hydrazonium iodides, and imines 287, as well as for A -(2-cyclohexen-l-ylidene)amines (enimines) 288. Similar to enol ethers267, electric-field effects are held responsible287. 

Catalytic Reduction of Oximes— Oximes may be reduced to primary amines in good yield by hydrogen in presence of nickel-kielselguhr (p. 172). (Am. Soc., 55, 1669). 

With aldehydes Addition compd. Oximes Oximes Nitrous acid nil... 

Figure 19 Distorted two-dimensional (4,4) network in nms-[Ni(L)4(OH2)2]Br2 2L (L = pyridine-4-aldoxime), propagated by oxime-oxime O-H O hydrogen bonds (cf. IX) [27c], Not shown are bromide anions and pyridine-4-aldoxime guest molecules, which are hydrogen-bonded to the 2D framework. Ni Ni separations are 16.3 A. Oxygen, nitrogen and key hydrogen atoms are shaded.

Deoximiation Oximes, oximic ethers, or oxime 0-acetates can be converted into the corresponding ketones by reaction with Fe,(CO)9 in CH,OH at 60°. This reaction proceeds particularly readily and in good yield with oxime acetates. 

The ability of silicon to stabilize positive charge to itself has been exploited in silicon-directed fragmentations of p-silyl oximes. Oxime 0-acetate (61) fragmented stereospecifically to the ( )-alkenic product in the presence of catalytic TMSOTf (equation 41). ... 

Isothiocyanate N-halo N-Hydroxy amine (oximes/oxime ether) N-oxide... 

Oximes.—Oximes of some saturated ketones are reduced by aqueous alkaline sodium borohydride under reflux to give the corresponding alcohols. Selective reduction of a 3,17-dioxime is possible, at C(3). a -Oximino-ketones afford diols. Diborane, in contrast, reduces oximes to give alkyl hydroxylamines a recent variant using sodium borohydride on silica gel in benzene gave the... 

The condensation of organolithium reagents (2 equiv.) with glyoxylate-derived oxime ethers (182) provides a direct method for the synthesis of a- -hydroxy amino acids (equation 22). Both glyoxylic acid and glyoxylamide oxime ethers are compatible with this process. A(>hydroxyaminoacetamides are also product in low/moderate yields by the addition of isonitriles to oximes (oxime ethers) analogous to the four component condensation described by Ugi. ... 

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