Heterocyclic compounds with bridgehead nitrogen atoms. Part 11. Formation of azocino[2,1,8-cd]pyrrolizines in the reactions of indolizines with dimethyl acetylenedicarboxylate
| العنوان: | Heterocyclic compounds with bridgehead nitrogen atoms. Part 11. Formation of azocino[2,1,8-cd]pyrrolizines in the reactions of indolizines with dimethyl acetylenedicarboxylate |
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| المؤلفون: | James W. Dick, Alexander J. Blake, Paul Strachan, Derek Leaver |
| المصدر: | Journal of the Chemical Society, Perkin Transactions 1. :2991 |
| بيانات النشر: | Royal Society of Chemistry (RSC), 1991. |
| سنة النشر: | 1991 |
| مصطلحات موضوعية: | Dimethyl acetylenedicarboxylate, chemistry.chemical_compound, Chemistry, Stereochemistry, X-ray crystallography, Molecule, Dehydrogenation, Crystal structure, Annulene, Ring (chemistry), Adduct |
| الوصف: | 5-Methyl-1-phenylindolizine and its 1 -acetyl derivative reacted with dimethyl acetylenedicarboxylate to give both 1 : 1 -and 1 : 2-adducts. UV and 1H NMR spectroscopy showed that these types of adducts are dihydro derivatives of pyrrolo[2,1,5-cd]indolizines and of azocino[2,1,8-cd]pyrrolizines, respectively. Contrary to previous claims, the 1 : 2-adducts similarly obtained from 6- and 7-methyl-2-phenylindolizines are also derivatives of the latter ring system; X-ray crystallography (of one such adduct) revealed stereochemical differences relative to the 1 : 2-adduct from 5-methyl-2-phenylindolizine, thus accounting for substantial associated differences in spectroscopic properties. Dehydrogenation products, previously claimed to be [2.3.4]cyclazines, are fully unsaturated azocino[2,1,8-cd] pyrrolizines. X-Ray crystallography showed that this hitherto unrecognised N-bridged [12] annulene ring system is markedly non-planar. |
| تدمد: | 1364-5463 0300-922X |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::773dd3ab9596e6ce1368f7916cde56f4 https://doi.org/10.1039/p19910002991 |
| رقم الأكسشن: | edsair.doi...........773dd3ab9596e6ce1368f7916cde56f4 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 13645463 0300922X |
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