Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles
Abstract
alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.
Keywords:
alpha,alpha-Dibromomethylketone / Bromophilic reaction / Nucleophilic substitution / Cascade reactionsSource:
Tetrahedron Letters, 2010, 51, 37, 4851-4855Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
- Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-MESTD-MPN2006-2010-142007)
DOI: 10.1016/j.tetlet.2010.07.057
ISSN: 0040-4039
WoS: 000281356700017
Scopus: 2-s2.0-77955848118
Collections
Institution/Community
IHTMTY - JOUR AU - Tatar, Jovana AU - Marković, Rade AU - Stojanović, Milovan AU - Baranac-Stojanović, Marija PY - 2010 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/703 AB - alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Tetrahedron Letters T1 - Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles VL - 51 IS - 37 SP - 4851 EP - 4855 DO - 10.1016/j.tetlet.2010.07.057 ER -
@article{ author = "Tatar, Jovana and Marković, Rade and Stojanović, Milovan and Baranac-Stojanović, Marija", year = "2010", abstract = "alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Tetrahedron Letters", title = "Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles", volume = "51", number = "37", pages = "4851-4855", doi = "10.1016/j.tetlet.2010.07.057" }
Tatar, J., Marković, R., Stojanović, M.,& Baranac-Stojanović, M.. (2010). Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles. in Tetrahedron Letters Oxford : Pergamon-Elsevier Science Ltd., 51(37), 4851-4855. https://doi.org/10.1016/j.tetlet.2010.07.057
Tatar J, Marković R, Stojanović M, Baranac-Stojanović M. Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles. in Tetrahedron Letters. 2010;51(37):4851-4855. doi:10.1016/j.tetlet.2010.07.057 .
Tatar, Jovana, Marković, Rade, Stojanović, Milovan, Baranac-Stojanović, Marija, "Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles" in Tetrahedron Letters, 51, no. 37 (2010):4851-4855, https://doi.org/10.1016/j.tetlet.2010.07.057 . .