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http://hdl.handle.net/11701/1961
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Поле DC | Значение | Язык |
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dc.contributor.author | Rostovskii, Nikolai V. | - |
dc.contributor.author | Novikov, Mikhail S. | - |
dc.contributor.author | Khlebnikov, Alexander F. | - |
dc.contributor.author | Starova, Galina L. | - |
dc.contributor.author | Avdontseva, Margarita S. | - |
dc.date.accessioned | 2016-04-07T21:31:37Z | - |
dc.date.available | 2016-04-07T21:31:37Z | - |
dc.date.issued | 2015-03 | - |
dc.identifier.citation | Beilstein J. Org. Chem. 2015, 11, 302–312 | en_GB |
dc.identifier.issn | 1860-5397 | - |
dc.identifier.uri | http://hdl.handle.net/11701/1961 | - |
dc.description.abstract | Strained azirinium ylides derived from 2H-azirines and α-diazoketones under Rh(II)-catalysis can undergo either irreversible ring opening across the N–C2 bond to 2-azabuta-1,3-dienes that further cyclize to 2H-1,4-oxazines or reversibly undergo a 1,5-cyclization to dihydroazireno[2,1-b]oxazoles. Dihydroazireno[2,1-b]oxazoles derived from 3-aryl-2H-azirines and 3-diazoacetylacetone or ethyl diazoacetoacetate are able to cycloadd to acetyl(methyl)ketene generated from 3-diazoacetylacetone under Rh(II) catalysis to give 4,6-dioxa-1-azabicyclo[3.2.1]oct-2-ene and/or 5,7-dioxa-1-azabicyclo[4.3.1]deca-3,8-diene-2-one derivatives. According to DFT calculations (B3LYP/6-31+G(d,p)), the cycloaddition can involve two modes of nucleophilic attack of the dihydroazireno[2,1-b]oxazole intermediate on acetyl(methyl)ketene followed by aziridine ring opening into atropoisomeric oxazolium betaines and cyclization. Azirinium ylides generated from 2,3-di- and 2,2,3-triaryl-substituted azirines give rise to only 2-azabuta-1,3-dienes and/or 2H-1,4-oxazines. | en_GB |
dc.language.iso | en | en_GB |
dc.publisher | Beilstein-Institut | en_GB |
dc.relation.ispartofseries | Beilstein Journal of Organic Chemistry;Vol. 15 | - |
dc.subject | nitrogen ylides | en_GB |
dc.subject | diazoketones | en_GB |
dc.subject | Azirines | en_GB |
dc.subject | 2H-1,4-oxazines | en_GB |
dc.subject | 2-azabuta-1,3-dienes | en_GB |
dc.title | Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization | en_GB |
dc.type | Article | en_GB |
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