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Download Nitrile Oxides, Nitrones & Nitronates in Organic Synthesis: by Henry Feuer PDF

By Henry Feuer

A finished systematization of present novel info in nitrile oxide chemistry, this ebook authoritatively covers systematic innovations presently utilized in the practise and usage of nitrile oxides, nitrones, and nitronates in natural synthesis. It covers components governing their balance and contains in-depth details on strong and volatile nitrile oxides. With contributions from major specialists, this can be a definitive reference for practising pros in natural or medicinal chemistry and a very good textual content for college students learning natural synthesis.

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On the basis of 13 C NMR, structures with Cs symmetry are proposed. These products result from addition of the nitrile oxide across a 6,6 ring fusion (254). O N CH2Me 89 Similarly, other cycloadducts of nitrile oxides with C60 were synthesized. The cycloadducts were characterized by 13 C NMR spectroscopy and high-resolution fast atom bombardment (FAB) mass spectrometry. It should be mentioned that X-ray structure determination of the 3-(9-anthryl)-4,5-dihydroisoxazole derivative of C60 , with CS2 included in the crystals, was achieved at 173 K (255).

Thus, a series of 3,5-diaryl-4,6-dioxo-3a,4,6,6a-tetrahydropyrrolo[3,4-d ]isoxazoles 95 was obtained by 1,3-dipolar cycloaddition of substituted benzonitrile oxides with N-(2,6-dialkylphenyl)maleimides. Certain compounds 95 showed bactericidal and fungicidal activity (264). R O O N N R2 O R1 95 1= R = R Me, Et; R = Me, R1 = Et; R = Ph, 2-MeOC6H4, 4-MeOC6H4, 4-ClC6H4, 2,4-Cl2C6H3, 3-O2NC6H4, 4-O2NC6H4, 4-FC6H4, 4-MeC6H4, 2-ClC6H4, 3,4-Cl2C6H3, 3,4-(OCH2O)C6H3, 3-MeOC6H4, 3,5,2-Cl2(MeO)C6H2, 3,4,5-(MeO)3C6H2 2 4-[Chloro(hydroxyimino)methyl]-3-phenyl-1,2,3-oxadiazolium-5-olate-(3phenylsydnone-4-carbohydroximoyl chloride) reacts in situ (through nitrile oxide) with N-arylmaleimides or 2-methyl-N-phenylmaleimide to give 5-aryl-3-(3phenylsydnon-4-yl)-3a,6a-dihydropyrrolo[3,4-d ]isoxazole-4,6-diones or 6amethyl-5-phenyl-3-(3-phenylsydnon-4-yl)-3a,6a-dihydropyrrolo[3,4-d]isoxazole4,6-diones, respectively (265).

The driving force of this reaction is stabilization by aromatization from isoxazoline derivatives to isoxazole-fused p-quinol derivatives (252). 5. Fullerenes Cycloaddition reactions are very popular for functionalization of fullerenes. Such reactions of fullerenes are compiled and discussed in detail in Reference 253. During the last 10 to 15 years, several communications appeared concerning [3 + 2] cycloaddition of nitrile oxides to fullerene C60 . Nitrile oxides, generated in the presence of C60 , form products of 1,3-cycloaddition, fullerene isoxazolines, for example, 89.

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