1,3-Dipolar addition of diazocyclopropane to eudesmane-type methylidene lactones and thermolysis of the resulting spiro-fused pyrazolines View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2012-02

AUTHORS

Yu. V. Tomilov, E. V. Revunov, E. V. Shulishov, V. V. Semenov

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. More... »

PAGES

280-286

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-012-0039-0

DOI

http://dx.doi.org/10.1007/s11172-012-0039-0

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1036917258


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