Reaction of levoglucosenone with diazocyclopropane |
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Authors: | Rafikov R R Novikov R A Shulishov E V Konyushkin L D Semenov V V Tomilov Yu V |
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Institution: | 1.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation ; |
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Abstract: | Depending of the reaction conditions, reaction of levoglucosenone with diazocyclopropane generated in situ from N-cyclopropyl- N-nitrosourea under the action of bases involved either the carbonyl group to give oxaspiropentane (MeONa/MeOH, s-30 °C), or
the double C=C bond to give l-pyrazoline (K2CO3, CH2Cl2, 5 °C). The latter readily reacted with diazocyclopropane at the C=O
group or added as a C-nucleophile in a regio-and stereoselective Michael reaction to the C=C bond of levoglucosenone. The
direction of reaction depended on the reactant ratio. The reaction of the levoglucosenone—diazomethane adduct with an excess
of levoglucosenone in the presence of a base yielded similar product bearing two levoglucosenone moieties. |
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