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Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals
dc.creator | Saičić, Radomir | |
dc.creator | Čeković, Živorad | |
dc.date.accessioned | 2018-11-22T00:00:32Z | |
dc.date.available | 2018-11-22T00:00:32Z | |
dc.date.issued | 1992 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/28 | |
dc.description.abstract | Sequential radical addition/5-exo-cyclization/β-elimination reactions, accomplished by thermally or photolytically induced decompositions of O-acyl derivatives of N-hydroxypyridine-2-thione or other thiohydroxamic esters of 6-phenylthio-4-hexenoic acid 11 in the presence of an excess of radicophilic olefins, afforded the 2-vinylcyclopentane derivatives 13 in 50-90% yields, while decompositions of thiohydroxami esters or 6-phenylthio-4-hexynoic acids 24, under the same experimental conditions and in the presence of electron deficient olefins, afforded the corresponding 2-vinylidenecyclopentane (2-exo-allenic cyclopentane) derivatives 2 (61-72%). However, when decompositions of thiohydroxamic esters 39 were carried out in boiling toluene solution without radicophilic olefins, 3-exo-cyclization took place and the corresponding 2-vinylcyclopropane derivatives 40 were obtained in 43-60% yields. © 1992. | en |
dc.rights | openAccess | |
dc.source | Tetrahedron | |
dc.subject | 3 + 2 cycloadditions | en |
dc.subject | 5-phenylthio-3-pentenyl radicals, thiohydroxamic esters of 6-phenylthio-4-hexenoic acids. | en |
dc.subject | sequential radical reactions | en |
dc.title | Sequential radical addition/cyclization/β-elimination reactions. 3-exo- and 5-exo-cycloaddition reactions of 5-phenylthio-3-pentenyl and 5-phenylthio-3-pentynyl radicals | en |
dc.type | article | |
dc.rights.license | ARR | |
dc.citation.volume | 48 | |
dc.citation.issue | 41 | |
dc.citation.spage | 8975 | |
dc.citation.epage | 8992 | |
dc.identifier.doi | 10.1016/S0040-4020(01)81996-7 | |
dc.citation.other | 48(41): 8975-8992 | |
dc.citation.rank | M21 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-0026705838 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/9580/26.pdf |