Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives
Само за регистроване кориснике
2001
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Regioselective a-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxo-thiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.
Кључне речи:
thiazolidines / halogenation / regiochemistry / rearrangementИзвор:
Tetrahedron, 2001, 57, 27, 5833-5841Издавач:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.1016/S0040-4020(01)00496-3
ISSN: 0040-4020
WoS: 000169540100017
Scopus: 2-s2.0-0035796409
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Džambaski, Z. AU - Baranac-Stojanović, Marija PY - 2001 UR - https://cherry.chem.bg.ac.rs/handle/123456789/460 AB - Regioselective a-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxo-thiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Tetrahedron T1 - Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives VL - 57 IS - 27 SP - 5833 EP - 5841 DO - 10.1016/S0040-4020(01)00496-3 ER -
@article{ author = "Marković, R. and Džambaski, Z. and Baranac-Stojanović, Marija", year = "2001", abstract = "Regioselective a-bromination of (Z)-5-substituted-2-alkylidene-4-oxothiazolidine derivatives affords, under mild experimental conditions, vinyl bromides 3 in good yields. They undergo rearrangement providing a highly efficient route to the stereodefined 4-oxo-thiazolidine derivatives possessing two fully delocalized exocyclic double bonds at C(2) and C(5) positions. A mechanism of this novel rearrangement reaction via base-promoted proton transfer from one carbanionic site to another, followed by the bromination-dehydrobromination sequence, is proposed. (C) 2001 Elsevier Science Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Tetrahedron", title = "Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives", volume = "57", number = "27", pages = "5833-5841", doi = "10.1016/S0040-4020(01)00496-3" }
Marković, R., Džambaski, Z.,& Baranac-Stojanović, M.. (2001). Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives. in Tetrahedron Pergamon-Elsevier Science Ltd, Oxford., 57(27), 5833-5841. https://doi.org/10.1016/S0040-4020(01)00496-3
Marković R, Džambaski Z, Baranac-Stojanović M. Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives. in Tetrahedron. 2001;57(27):5833-5841. doi:10.1016/S0040-4020(01)00496-3 .
Marković, R., Džambaski, Z., Baranac-Stojanović, Marija, "Stereo- and regiocontrol of electrophile-initiated rearrangement of push-pull 5-substituted 4-oxothiazolidine derivatives" in Tetrahedron, 57, no. 27 (2001):5833-5841, https://doi.org/10.1016/S0040-4020(01)00496-3 . .