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
Apstrakt
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.
Ključne reči:
3 + 2 cycloadditions / 5-phenylthio-3-pentenyl radicals, thiohydroxamic esters of 6-phenylthio-4-hexenoic acids. / sequential radical reactionsIzvor:
Tetrahedron, 1992, 48, 41, 8975-8992Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Saičić, Radomir AU - Čeković, Živorad PY - 1992 UR - https://cherry.chem.bg.ac.rs/handle/123456789/28 AB - 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. T2 - Tetrahedron T1 - 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 VL - 48 IS - 41 SP - 8975 EP - 8992 DO - 10.1016/S0040-4020(01)81996-7 ER -
@article{ author = "Saičić, Radomir and Čeković, Živorad", year = "1992", 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.", journal = "Tetrahedron", 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", volume = "48", number = "41", pages = "8975-8992", doi = "10.1016/S0040-4020(01)81996-7" }
Saičić, R.,& Čeković, Ž.. (1992). 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. in Tetrahedron, 48(41), 8975-8992. https://doi.org/10.1016/S0040-4020(01)81996-7
Saičić R, Čeković Ž. 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. in Tetrahedron. 1992;48(41):8975-8992. doi:10.1016/S0040-4020(01)81996-7 .
Saičić, Radomir, Čeković, Živorad, "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" in Tetrahedron, 48, no. 41 (1992):8975-8992, https://doi.org/10.1016/S0040-4020(01)81996-7 . .