TY  - JOUR
AU  - Sazonov, P. K.
AU  - Džambaski, Zdravko
AU  - Shtern, M. M.
AU  - Marković, Rade
AU  - Beletskaya, I. P.
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/927
AB  - 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.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation
VL  - 52
IS  - 1
SP  - 29
EP  - 33
DO  - 10.1016/j.tetlet.2010.10.112
ER  - 

@article{
author = "Sazonov, P. K. and Džambaski, Zdravko and Shtern, M. M. and Marković, Rade and Beletskaya, I. P.",
year = "2011",
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.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation",
volume = "52",
number = "1",
pages = "29-33",
doi = "10.1016/j.tetlet.2010.10.112"
}

Sazonov, P. K., Džambaski, Z., Shtern, M. M., Marković, R.,& Beletskaya, I. P.. (2011). Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 52(1), 29-33.
https://doi.org/10.1016/j.tetlet.2010.10.112

Sazonov PK, Džambaski Z, Shtern MM, Marković R, Beletskaya IP. Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation. in Tetrahedron Letters. 2011;52(1):29-33.
doi:10.1016/j.tetlet.2010.10.112 .

Sazonov, P. K., Džambaski, Zdravko, Shtern, M. M., Marković, Rade, Beletskaya, I. P., "Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation" in Tetrahedron Letters, 52, no. 1 (2011):29-33,
https://doi.org/10.1016/j.tetlet.2010.10.112 . .