Acetophenone 4-nitro-, oxime

S612). However, more work is needed to determine its full utility. Table 16 lists the types of isoxazoles synthesized from the condensation of 1,4-dilithio oximes (358) and 2-nitro-acetophenone oximes with electrophiles. 

Sodium perborate in acetic acid converts oximes into nitro compounds thus acetophenone oxime yields 52% of PhCHMeN02403. Nitroalkanes and nitroarenes are obtained from isocyanates and dimethyldioxirane (equation 122)404. 

A possible synthesis of the extensively studied 4,5-dichloro-l,2,3-dithiazolium chloride (Appel salt) analogs (see next section) was found in the reaction of acetophenone oxime and its 4-nitro derivative with S2CI2 (1994H1827, 1997BSB605 Scheme 73). 

Acetophenone oxime and its 4-nitro derivative gave with S2Cl2 the l,2,3-dithiazolium chlorides 135. These are analogs of Appel salt 20 which were not isolated but converted to the 5-arylimino derivatives 136 by the reaction with arylamines (Scheme 21) <1997BSB605>. 

CAN-mediated nitration provides a convenient route for the introduction of a nitro group into a variety of substrates. Alkenes on treatment with an excess of sodium nitrite and CAN in chloroform under sonication afford nitroalkenes. When acetonitrile is used as the solvent, nitroacetamidation occurs in a Ritter-type fashion. However, the attempted nitroacetamidation of cyclo-pentene-1 -carboxaldehyde under similar conditions resulted in the formation of an unexpected dinitro-oxime compound. A one-pot synthesis of 3-acetyl- or 3-benzoylisoxazole derivatives by reaction of alkenes (or alkynes) with CAN in acetone or acetophenone has been reported. The proposed mechanism involves a-nitration of the solvent acetone, oxidation to generate the nitrile oxide, and subsequent 1,3-dipolar cycloaddition with alkenes or alkynes. The nitration of aromatic compounds such as carbozole, naphthalene, and coumarins by CAN has also been investigated. As an example, coumarin on treatment with 1 equiv of CAN in acetic acid gives 6-nitrocoumarin in 92% yield. ... 

Alcohols from oxo compds. 20 eqs. NaBH4 added to a soln. of 5 eqs. ZrC in THF at room temp, under N2, a soln. of 4 eqs. acetophenone in the same solvent added, and the mixture stirred at room temp, for 5 h - 1-phenylethanol. Y 96%. ZrCl4 is inexpensive, easy to use, and does not affect ar. nitro compds. and bromides. F.e., also reduction of carboxylic acids, esters and halides to prim, alcohols, and amides, oximes, alkoximes, nitriles, and imines to amines, s. S. Itsuno et al.. Synthesis 1988, 995-6. 

Nitro-4-methoxy-x-benzaidoxim-O-methyl ther 8 II 78. 3-Nitro-4-methoxy- -benzaldoxim-0-methylather 8 II78. co-Nitro-I-methoxy-acetophenon-oxim 8, 89, II 87. 

Also obtained by reaction of boiling 20% aqueous hydrochloric acid on 2-hydroxy-3-nitro-acetophenone oxime [2076]. 

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