Abstract
Diazocyclopropane attacks the carbonyl group of 6,8-dioxabicyclo[3.2.1]octan-4-one or 7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one, saturated derivatives of levoglucosenone, to form the corresponding stereoisomeric oxaspiropentanes. In the case of the strained tricyclononane, 5R-isomer isomerizes under the reaction conditions into spiro-fused cyclobutanone. For this ketone, the formation of homologation products, i.e., the respective regioisomeric spiro-[8,10-dioxatricyclo[5.2.1.02,4]decane-6(5),1′-cyclopropan]-5(6)-ones, is also observed.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2371–2377, December, 2009.
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Rafikov, R.R., Novikov, R.A., Shulishov, E.V. et al. Reactions of diazocyclopropane with hydrogenated and cyclopropanated levoglucosenone analogs. Russ Chem Bull 58, 2449–2455 (2009). https://doi.org/10.1007/s11172-009-0343-5
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DOI: https://doi.org/10.1007/s11172-009-0343-5