Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds
Abstract
An efficient method for the formation of α-carbonyl-monosubstituted acetophenones from ortho-methoxy- and ortho-hydroxy-α,α-dibromoacetophenones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of α,α-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones.
Source:
Tetrahedron Letters, 2009, 50, 6, 700-703Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
DOI: 10.1016/j.tetlet.2008.11.104
ISSN: 0040-4039
WoS: 000263310800025
Scopus: 2-s2.0-57749201586
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IHTMTY - JOUR AU - Tatar, Jovana AU - Baranac-Stojanović, Marija AU - Stojanović, Milovan AU - Marković, Rade PY - 2009 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/595 AB - An efficient method for the formation of α-carbonyl-monosubstituted acetophenones from ortho-methoxy- and ortho-hydroxy-α,α-dibromoacetophenones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of α,α-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Tetrahedron Letters T1 - Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds VL - 50 IS - 6 SP - 700 EP - 703 DO - 10.1016/j.tetlet.2008.11.104 ER -
@article{ author = "Tatar, Jovana and Baranac-Stojanović, Marija and Stojanović, Milovan and Marković, Rade", year = "2009", abstract = "An efficient method for the formation of α-carbonyl-monosubstituted acetophenones from ortho-methoxy- and ortho-hydroxy-α,α-dibromoacetophenones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of α,α-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Tetrahedron Letters", title = "Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds", volume = "50", number = "6", pages = "700-703", doi = "10.1016/j.tetlet.2008.11.104" }
Tatar, J., Baranac-Stojanović, M., Stojanović, M.,& Marković, R.. (2009). Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds. in Tetrahedron Letters Oxford : Pergamon-Elsevier Science Ltd., 50(6), 700-703. https://doi.org/10.1016/j.tetlet.2008.11.104
Tatar J, Baranac-Stojanović M, Stojanović M, Marković R. Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds. in Tetrahedron Letters. 2009;50(6):700-703. doi:10.1016/j.tetlet.2008.11.104 .
Tatar, Jovana, Baranac-Stojanović, Marija, Stojanović, Milovan, Marković, Rade, "Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds" in Tetrahedron Letters, 50, no. 6 (2009):700-703, https://doi.org/10.1016/j.tetlet.2008.11.104 . .