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- W2952854163 abstract "Addition von Diazoalkanen an die tetrahalogenierten Cyclobutene 1–3, fuhrt zu 6,6,7,7-Tetrahalogeno-2,3-diazabicyclo[3.2.0]hept-2-enen 4–8, deren Konstitution und Stereochemie auf NMR-spektroskopischem Weg ermittelt wurde. Durch thermische Zersetzung der Bicyclen 4,5 und 8 in siedendem Toluol erhalt man in guten Ausbeuten Tetrahalogenobicyclo-[2.1.0]pentane 9,10 und 12. Unter gleichen Bedingungen entstehen aus 7 in stereospezifischer Reaktion 11 sowie geringe Mengen des Cyclobutens 13. Mittels Natriummethylat werden die Bicyclen 9–11 zu den Cyclobutenen 14, 15 abgebaut; unter dem Einflus von konz. Schwefelsaure entsteht aus 10 je nach Reaktionsbedingungen das Cyclobutendion 16 bzw. ein Gemisch der Cyclopentenone 18 und 19.Stereochemistry and Reactivity of Tetrahalogenated 2,3-Diazabicyclo[3.2.0]hept-2-enes and Bicyclo [2.1.0] pentanesThe addition of diazoalkanes to tetrahalogenated cyclobutenes 1–3 leads to 6,6,7,7-tetrahalo-2,3-diazabicyclo[3.2.0]hept-2-enes 4–8, the structure and stereochemistry of which are determined by means of n. m. r. spectroscopy. Thermal decomposition of 4, 5, and 8 in boiling toluene affords the tetrahalobicyclo[2.1.0]pentanes 9, 10, and 12 in good yields. Under the same conditions 7 decomposes in a stereospecific manner to form 11 and small amounts of 13. Sodium methoxide converts 9–11 into the cyclobutenes 14 and 15. Under the influence of sulfuric acid 10 forms the cyclobutenedione 16 or a mixture of cyclopentenones 18, 19 depending on the reaction conditions." @default.
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- W2952854163 date "1974-05-07" @default.
- W2952854163 modified "2023-09-27" @default.
- W2952854163 title "ChemInform Abstract: STEREOCHEMIE UND REAKTIVES VERHALTEN TETRAHALOGENIERTER 2,3-DIAZABICYCLO(3,2,0)HEPT-2-ENE UND BICYCLO(2,1,0)PENTANE" @default.
- W2952854163 cites W2024118267 @default.
- W2952854163 doi "https://doi.org/10.1002/chin.197418228" @default.
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