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Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles

Authorized Users Only
2010
Authors
Tatar, Jovana
Marković, Rade
Stojanović, Milovan
Baranac-Stojanović, Marija
Article (Published version)
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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 reactions
Source:
Tetrahedron Letters, 2010, 51, 37, 4851-4855
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-142007)

DOI: 10.1016/j.tetlet.2010.07.057

ISSN: 0040-4039

WoS: 000281356700017

Scopus: 2-s2.0-77955848118
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/703
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