1,3-Dipolar addition of diazocyclopropane to eudesmane-type methylidene lactones and thermolysis of the resulting spiro-fused pyrazolines Full article
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Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285 |
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| Output data | Year: 2012, Volume: 61, Number: 2, Pages: 280-286 Pages count : 7 DOI: 10.1007/s11172-012-0039-0 | ||
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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.
Cite:
Tomilov Y.V.
, Revunov E.V.
, Shulishov E.V.
, Semenov V.V.
1,3-Dipolar addition of diazocyclopropane to eudesmane-type methylidene lactones and thermolysis of the resulting spiro-fused pyrazolines
Russian Chemical Bulletin. 2012. V.61. N2. P.280-286. DOI: 10.1007/s11172-012-0039-0 WOS Scopus OpenAlex
1,3-Dipolar addition of diazocyclopropane to eudesmane-type methylidene lactones and thermolysis of the resulting spiro-fused pyrazolines
Russian Chemical Bulletin. 2012. V.61. N2. P.280-286. DOI: 10.1007/s11172-012-0039-0 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000312068000008 |
| Scopus: | 2-s2.0-84877037300 |
| OpenAlex: | W2097607806 |