2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry
Само за регистроване кориснике
2013
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.
Кључне речи:
2-Alkylidene-4-oxothiazolidine / Sulfoxide / Diastereoselectivity / Density functional calculations / CH center dot center dot center dot O hydrogen bondsИзвор:
Tetrahedron, 2013, 69, 31, 6436-6447Издавач:
- Oxford : Pergamon-Elsevier Science Ltd
Финансирање / пројекти:
- Експериментална и теоријска проучавања реактивности и биолошка активност стереодефинисаних тиазолидина и синтетичких аналога (RS-172020)
- Deutscher Akademischer Austauschdienst (DAAD) [504 252 70]
DOI: 10.1016/j.tet.2013.05.087
ISSN: 0040-4020
WoS: 000321231700013
Scopus: 2-s2.0-84879225906
Институција/група
IHTMTY - JOUR AU - Džambaski, Zdravko AU - Marković, Rade AU - Kleinpeter, Erich AU - Baranac-Stojanović, Marija PY - 2013 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1344 AB - A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Tetrahedron T1 - 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry VL - 69 IS - 31 SP - 6436 EP - 6447 DO - 10.1016/j.tet.2013.05.087 ER -
@article{ author = "Džambaski, Zdravko and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija", year = "2013", abstract = "A series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Tetrahedron", title = "2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry", volume = "69", number = "31", pages = "6436-6447", doi = "10.1016/j.tet.2013.05.087" }
Džambaski, Z., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2013). 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry. in Tetrahedron Oxford : Pergamon-Elsevier Science Ltd., 69(31), 6436-6447. https://doi.org/10.1016/j.tet.2013.05.087
Džambaski Z, Marković R, Kleinpeter E, Baranac-Stojanović M. 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry. in Tetrahedron. 2013;69(31):6436-6447. doi:10.1016/j.tet.2013.05.087 .
Džambaski, Zdravko, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry" in Tetrahedron, 69, no. 31 (2013):6436-6447, https://doi.org/10.1016/j.tet.2013.05.087 . .