1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group
Apstrakt
The acid catalysed ring opening of tertiary cyclopropylmethanols 1 (R = H, vinyl, Ph), possessing a phenylthio group on the adjacent carbon atom proceeds, regioselectively and homoallylic halides 2 are obtained in 49 - 86% yields. Depending on the structure of 1 (R= Ph, SPh) and the acid used the cyclopropane ring opening follows the 1,3-migration of phenylthio group and the corresponding 1-halo-3-phenylthio-4-pentene derivatives 3 are obtained in 54-76% yields.
Ključne reči:
1,3-migration of phenylthio group / Cyclopropane ring opening / Cyclopropylcarbinyl carbocationIzvor:
Journal of the Serbian Chemical Society, 1996, 61, 10, 841-848Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Saičić, Radomir AU - Badić, J. AU - Čeković, Živorad PY - 1996 UR - https://cherry.chem.bg.ac.rs/handle/123456789/61 AB - The acid catalysed ring opening of tertiary cyclopropylmethanols 1 (R = H, vinyl, Ph), possessing a phenylthio group on the adjacent carbon atom proceeds, regioselectively and homoallylic halides 2 are obtained in 49 - 86% yields. Depending on the structure of 1 (R= Ph, SPh) and the acid used the cyclopropane ring opening follows the 1,3-migration of phenylthio group and the corresponding 1-halo-3-phenylthio-4-pentene derivatives 3 are obtained in 54-76% yields. T2 - Journal of the Serbian Chemical Society T1 - 1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group VL - 61 IS - 10 SP - 841 EP - 848 UR - https://hdl.handle.net/21.15107/rcub_cherry_61 ER -
@article{ author = "Saičić, Radomir and Badić, J. and Čeković, Živorad", year = "1996", abstract = "The acid catalysed ring opening of tertiary cyclopropylmethanols 1 (R = H, vinyl, Ph), possessing a phenylthio group on the adjacent carbon atom proceeds, regioselectively and homoallylic halides 2 are obtained in 49 - 86% yields. Depending on the structure of 1 (R= Ph, SPh) and the acid used the cyclopropane ring opening follows the 1,3-migration of phenylthio group and the corresponding 1-halo-3-phenylthio-4-pentene derivatives 3 are obtained in 54-76% yields.", journal = "Journal of the Serbian Chemical Society", title = "1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group", volume = "61", number = "10", pages = "841-848", url = "https://hdl.handle.net/21.15107/rcub_cherry_61" }
Saičić, R., Badić, J.,& Čeković, Ž.. (1996). 1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group. in Journal of the Serbian Chemical Society, 61(10), 841-848. https://hdl.handle.net/21.15107/rcub_cherry_61
Saičić R, Badić J, Čeković Ž. 1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group. in Journal of the Serbian Chemical Society. 1996;61(10):841-848. https://hdl.handle.net/21.15107/rcub_cherry_61 .
Saičić, Radomir, Badić, J., Čeković, Živorad, "1,3-Migration of phenylthio group in the rearrangement of tertiary cyclopropylmethanols possessing an α-phenylthio group" in Journal of the Serbian Chemical Society, 61, no. 10 (1996):841-848, https://hdl.handle.net/21.15107/rcub_cherry_61 .