1985
DOI: 10.1246/bcsj.58.2519
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A New Synthetic Method of Alkyl Carbonocyanidate N-Oxides

Abstract: A thermal decomposition of dimethyl nitromalonate to bis(carbomethoxy)furoxan was observed at about 170 °C. In the presence of dipolarophiles, an intermediate, methyl carbonocyanidate N-oxide MeOCOC≡N→O, could be trapped as cycloadducts in good yields by the 1,3-dipolar cycloaddition. Treatment of dimethyl nitromalonate in mesitylene at the refluxing temperature resulted in a formation of methyl 2-(hydroxyimino)-2-(2,4,6-trimethylphenyl)acetate.

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Cited by 26 publications
(15 citation statements)
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“…The above disadvantage was overcome by using excess dipolarophile, and the yield of 8a in this case was improved up to 72% (run 6). When THF was used as a co-solvent in the present reaction, 10 the yield of 8a was comparable to that mentioned in the previous sentence (run 7); however, acetonitrile was preferred because of the high solubility of 5a in this solvent. Other dipolarophiles 7b-d and 10a-l were subjected to cycloaddition under the optimized conditions used for 20 ethynylbenzene 7a ( Table 2, run 1).…”
supporting
confidence: 68%
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“…The above disadvantage was overcome by using excess dipolarophile, and the yield of 8a in this case was improved up to 72% (run 6). When THF was used as a co-solvent in the present reaction, 10 the yield of 8a was comparable to that mentioned in the previous sentence (run 7); however, acetonitrile was preferred because of the high solubility of 5a in this solvent. Other dipolarophiles 7b-d and 10a-l were subjected to cycloaddition under the optimized conditions used for 20 ethynylbenzene 7a ( Table 2, run 1).…”
supporting
confidence: 68%
“…The organic layer was concentrated, and the residue was subjected to column chromatography to 5 afford a mixture of 18 and 3d (eluted with hexane/CHCl 3 = 2/1, 23 mg, yield of 18; 18%, yield of 3d; 12%) and nitroenamine 18 (eluted with hexane/CHCl 3 = 1/1, 30 mg, 0.23 mmol, yield 46%). Although further purification of 3d was attempted by column chromatography again, impurity 10 could not be removed. The structural determination was performed by comparing spectral data with those of 3e, which was prepared from commercially available ethyl nitroacetate and ethyl isocyanate.…”
Section: Experimental Generalmentioning
confidence: 99%
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