Abstract
Reactions of alanto-, isoalanto-, and alloalantolactones, which are unsaturated eudesmane-type lactones, with diazocyclopropane generated in situ from N-cyclopropyl-N-nitrosourea under the action of sodium methoxide proceed alike, are highly regio- and stereoselective, and always give spiro-fused pyrazolines via cycloaddition to the exocyclic double bond of the methylidene group of the lactone ring. Their thermolysis at 195–210 °C results in elimination of molecular nitrogen, mainly yielding spiropentane-containing lactones. Minor thermolysis products (10–12%) are isomeric 13-cyclopropyl lactones.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 280–286, February, 2012.
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Tomilov, Y.V., Revunov, E.V., Shulishov, E.V. et al. 1,3-Dipolar addition of diazocyclopropane to eudesmane-type methylidene lactones and thermolysis of the resulting spiro-fused pyrazolines. Russ Chem Bull 61, 280–286 (2012). https://doi.org/10.1007/s11172-012-0039-0
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DOI: https://doi.org/10.1007/s11172-012-0039-0