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Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation

Authorized Users Only
2011
Authors
Sazonov, P. K.
Džambaski, Zdravko
Shtern, M. M.
Marković, Rade
Beletskaya, I. P.
Article (Published version)
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Abstract
Bromophilic attack by the transition metal carbonyl anion, [Re(CO)(5)]Na (pK(a) = 21.1), on 2-(1-bromoalkylidene)thiazolidin-4-ones is significantly faster than abstraction of an acidic lactam hydrogen (pK(a) similar to 17-18), when the generated carbanion is stabilized by an alpha-CN or alpha-PhCO group. The bromophilic reaction of 2-(1-bromoalkylidene)thiazolidin-4-one, having an alpha-CN electron-withdrawing group, resulted in formation of a new metallacyclic anionic complex. With less reactive vinyl bromides, containing an alpha-CONHPh or alpha-CO(2)Et group, only deprotonation is observed. The role of the metal carbonyl anion is highlighted by a comparison with the 9-methylfluorenide carbanion (pK(a) of 9-methylfluorene is 22.3), which reacts exclusively via a deprotonation pathway.
Keywords:
Halogenophilic reactions / Proton transfer / 2-(1-Bromoalkylidene)thiazolidin-4-ones / Metal carbonyl anions
Source:
Tetrahedron Letters, 2011, 52, 1, 29-33
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Russian Federation - HLLI-4365.2010.3
  • RAS - 1-OX
  • Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-142007)

DOI: 10.1016/j.tetlet.2010.10.112

ISSN: 0040-4039

WoS: 000286789100005

Scopus: 2-s2.0-78649872730
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/927
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IHTM

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