Preparation of cyclopropanone 2,2,2-trifluoroethoxy hemiacetals via oxyallyl cation
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Cyclopropanone / hemiacetals / 2,2,2-trifluoroethanol / oxyallyl cation / Favorskii rearrangement / mechanism / DFTIzvor:
ARKIVOC - Online Journal of Organic Chemistry, 2024, 2024, 2Izdavač:
- ARKAT USA, Inc.
Finansiranje / projekti:
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-MESTD-inst-2020-200026)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200168 (Univerzitet u Beogradu, Hemijski fakultet) (RS-MESTD-inst-2020-200168)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200288 (Inovacioni centar Hemijskog fakulteta u Beogradu doo) (RS-MESTD-inst-2020-200288)
Napomena:
- Dedicated to Professor Samir Zard, with admiration for his outstanding scientific achievements.
Institucija/grupa
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 . .