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O H H S Ar′ N Ph Ar′ O Ar S N O N Ph 119 120 Ar = 2,4,6-Me2C6H2, 2,6-Cl2C6H3; Ar′ = Ph, p-MeC6H4 Substituted 3-alkenyl-5-methylene-4,5-dihydro-1H -pyrazole 121 reacts with 4-MeC6 H4 CNO to give the spiro compound 122 (Ar = 4-C6 H4 Me) (284). 44 NITRILE OXIDES Ph2CHCO N N Ph2CHCO O2CAr H2C Me N Ph Me N N O Ph Ar Me Me O2CAr Ph Ph 122 121 The cycloaddition of nitrile oxides to 4-methylenetetrahydrothiopyran proceeds regioselectively with the formation of spiro-substituted isoxazolines 123 (R = H, Cl, NO2 ).
15) on addition to nitrile oxides, which are generated from the corresponding hydroximoyl chlorides (117). The 1,3-dipoles were generated by the addition of Et3 N in 20% excess. Only imidazole was basic enough to generate a nitrile oxide in the absence of triethylamine. Due to prototropic tautomerism, reactions of triazoles and tetrazoles led to mixtures of two isomers. With unsubstituted pyrazole and imidazole only one hydroximoylazole was formed (117). Interesting examples of the addition of N-nucleophiles to nitrile oxides are syntheses of chelated Z -amidoxime, N-[2-(dimethylaminomethyl)phenyl]mesitylenecarboamidoxime (118), and pyranosyl amidoximes (119) from the respective nitrile oxides and amines.
Cl Cl NOH C NOAlCl3 Cl 30 C Ph Cl 31 Nitrile oxide–BF3 complexes can also be used as electrophilic moieties with aromatic systems. Introducing BF3 into a mixture of 2,6-dichlorobenzonitrile oxide and mesitylene in hexane, gave 88% Z -2 ,6 -dichloro-2,4,6-trimethylbenzophenone oxime (128). Nitrile oxides react in situ with formaldehyde dimethylhydrazone (129) to give oxime-hydrazones RC(:NOH)CH:NNMe2 (R = 4-O2 NC6 H4 , MeCO, MeC (:NOH)). The reaction is performed on treatment of oximes with CH2 :NNMe2 in the presence of Et3 N without isolation of the intermediate nitrile oxides.