Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Hemiacetals of cyclopropanone can be isolated and stocked, contrary to their highly reactive parent ketone. However, they are not readily converted to cyclopropanone, which limits their use as its synthetic equivalents. 2,2,2-trifluoroethoxy hemiacetals are expected to be better cyclopropanone surrogates, however, they have never been prepared, so far. We show that oxyallyl cations with a heteroatom in the -position can be intercepted with 2,2,2-trifluoroethanol, with formation of cyclopropanone trifluoroethoxy hemiacetals stable enough to be isolated, purified and characterized. These species can serve as synthetic equivalents of cyclopropanone under mild conditions.
Кључне речи:
Cyclopropanone / hemiacetals / 2,2,2-trifluoroethanol / oxyallyl cation / Favorskii rearrangement / mechanism / DFTИзвор:
ARKIVOC - Online Journal of Organic Chemistry, 2024, 2024, 2Издавач:
- ARKAT USA, Inc.
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200288 (Иновациони центар Хемијског факултета у Београду доо) (RS-MESTD-inst-2020-200288)
Напомена:
- Dedicated to Professor Samir Zard, with admiration for his outstanding scientific achievements.
Институција/група
IHTMTY - JOUR AU - Trmčić, Milena AU - Vulović, Bojan AU - Zlatar, Matija AU - Saičić, Radomir N. PY - 2024 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/7041 AB - Hemiacetals of cyclopropanone can be isolated and stocked, contrary to their highly reactive parent ketone. However, they are not readily converted to cyclopropanone, which limits their use as its synthetic equivalents. 2,2,2-trifluoroethoxy hemiacetals are expected to be better cyclopropanone surrogates, however, they have never been prepared, so far. We show that oxyallyl cations with a heteroatom in the -position can be intercepted with 2,2,2-trifluoroethanol, with formation of cyclopropanone trifluoroethoxy hemiacetals stable enough to be isolated, purified and characterized. These species can serve as synthetic equivalents of cyclopropanone under mild conditions. PB - ARKAT USA, Inc. T2 - ARKIVOC - Online Journal of Organic Chemistry T1 - Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation VL - 2024 IS - 2 DO - 10.24820/ark.5550190.p012.123 ER -
@article{ author = "Trmčić, Milena and Vulović, Bojan and Zlatar, Matija and Saičić, Radomir N.", year = "2024", abstract = "Hemiacetals of cyclopropanone can be isolated and stocked, contrary to their highly reactive parent ketone. However, they are not readily converted to cyclopropanone, which limits their use as its synthetic equivalents. 2,2,2-trifluoroethoxy hemiacetals are expected to be better cyclopropanone surrogates, however, they have never been prepared, so far. We show that oxyallyl cations with a heteroatom in the -position can be intercepted with 2,2,2-trifluoroethanol, with formation of cyclopropanone trifluoroethoxy hemiacetals stable enough to be isolated, purified and characterized. These species can serve as synthetic equivalents of cyclopropanone under mild conditions.", publisher = "ARKAT USA, Inc.", journal = "ARKIVOC - Online Journal of Organic Chemistry", title = "Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation", volume = "2024", number = "2", doi = "10.24820/ark.5550190.p012.123" }
Trmčić, M., Vulović, B., Zlatar, M.,& Saičić, R. N.. (2024). Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation. in ARKIVOC - Online Journal of Organic Chemistry ARKAT USA, Inc.., 2024(2). https://doi.org/10.24820/ark.5550190.p012.123
Trmčić M, Vulović B, Zlatar M, Saičić RN. Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation. in ARKIVOC - Online Journal of Organic Chemistry. 2024;2024(2). doi:10.24820/ark.5550190.p012.123 .
Trmčić, Milena, Vulović, Bojan, Zlatar, Matija, Saičić, Radomir N., "Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation" in ARKIVOC - Online Journal of Organic Chemistry, 2024, no. 2 (2024), https://doi.org/10.24820/ark.5550190.p012.123 . .