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Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds

Authorized Users Only
2009
Authors
Tatar, Jovana
Baranac-Stojanović, Marija
Stojanović, Milovan
Marković, Rade
Article (Published version)
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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, 700-703
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-142007)

DOI: 10.1016/j.tetlet.2008.11.104

ISSN: 0040-4039

WoS: 000263310800025

Scopus: 2-s2.0-57749201586
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/595
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