Reaction of levoglucosenone with diazocyclopropane

Reaction of levoglucosenone with diazocyclopropane Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2009, Volume: 58, Number: 9, Pages: 1927-1933 Pages count : 7 DOI: 10.1007/s11172-009-0263-4

Authors

Rafikov R.R. ¹ , Novikov R.A. ¹ , Shulishov E.V. ¹ , Konyushkin L.D. ¹ , Semenov V.V. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

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.

Rafikov R.R. , Novikov R.A. , Shulishov E.V. , Konyushkin L.D. , Semenov V.V. , Tomilov Y.V.
Reaction of levoglucosenone with diazocyclopropane
Russian Chemical Bulletin. 2009. V.58. N9. P.1927-1933. DOI: 10.1007/s11172-009-0263-4 WOS Scopus OpenAlex

Web of science:	WOS:000283500400022
Scopus:	2-s2.0-77956607792
OpenAlex:	W2042737165

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OpenAlex	6
Scopus	4
Web of science	8