TY  - JOUR
AU  - Damljanovic, Ivan
AU  - Vukicevic, Mirjana
AU  - Manojlović, Dragan D.
AU  - Šojić, Nešo
AU  - Buriez, Olivier
AU  - Vukicevic, Rastko D.
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1042
AB  - The electrochemical bromination of 3,4.6-tri-O-acetyl-D-glucal (1) has been investigated in dimethyl sulfoxide (DMSO) by cyclic voltammetry and preparative-scale electrolyses. In this solvent, the bromination involves a bromine-DMSO complex of the type [DMSO-Br](+) Br(-) whose reactivity towards 1 was clearly evidenced by cyclic voltammetry. Importantly, only the monobrominated glucose and mannose derivatives were obtained from electrolyses. This specific behavior was attributed to the nucleophilicity of DMSO that may react with the oxocarbenium intermediate preventing thus a possible second bromination of the transient species. The gluco/manno ratio, roughly equal to 30/70, indicated an electrophilic attack by [DMSO-Br](+) Br(-) preferentially from the beta side of the starting glycal for steric reasons. The treatment of the crude product obtained after the end of the electrolyses with acetic anhydride allowed the preparation of derivatives in which the anomeric carbon bears an acetoxy group. Based on both the cyclic voltammetry experiments and preparative-scale electrolyses, a mechanism is proposed for the bromination of peracetylated D-glucal in DMSO. These new and original results are of high interest in carbohydrate chemistry and especially for the preparation of new valuable oligosaccharides. (C) 2009 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Electrochimica Acta
T1  - Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity
VL  - 55
IS  - 3
SP  - 965
EP  - 969
DO  - 10.1016/j.electacta.2009.09.057
ER  - 

@article{
author = "Damljanovic, Ivan and Vukicevic, Mirjana and Manojlović, Dragan D. and Šojić, Nešo and Buriez, Olivier and Vukicevic, Rastko D.",
year = "2010",
abstract = "The electrochemical bromination of 3,4.6-tri-O-acetyl-D-glucal (1) has been investigated in dimethyl sulfoxide (DMSO) by cyclic voltammetry and preparative-scale electrolyses. In this solvent, the bromination involves a bromine-DMSO complex of the type [DMSO-Br](+) Br(-) whose reactivity towards 1 was clearly evidenced by cyclic voltammetry. Importantly, only the monobrominated glucose and mannose derivatives were obtained from electrolyses. This specific behavior was attributed to the nucleophilicity of DMSO that may react with the oxocarbenium intermediate preventing thus a possible second bromination of the transient species. The gluco/manno ratio, roughly equal to 30/70, indicated an electrophilic attack by [DMSO-Br](+) Br(-) preferentially from the beta side of the starting glycal for steric reasons. The treatment of the crude product obtained after the end of the electrolyses with acetic anhydride allowed the preparation of derivatives in which the anomeric carbon bears an acetoxy group. Based on both the cyclic voltammetry experiments and preparative-scale electrolyses, a mechanism is proposed for the bromination of peracetylated D-glucal in DMSO. These new and original results are of high interest in carbohydrate chemistry and especially for the preparation of new valuable oligosaccharides. (C) 2009 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Electrochimica Acta",
title = "Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity",
volume = "55",
number = "3",
pages = "965-969",
doi = "10.1016/j.electacta.2009.09.057"
}

Damljanovic, I., Vukicevic, M., Manojlović, D. D., Šojić, N., Buriez, O.,& Vukicevic, R. D.. (2010). Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity. in Electrochimica Acta
Pergamon-Elsevier Science Ltd, Oxford., 55(3), 965-969.
https://doi.org/10.1016/j.electacta.2009.09.057

Damljanovic I, Vukicevic M, Manojlović DD, Šojić N, Buriez O, Vukicevic RD. Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity. in Electrochimica Acta. 2010;55(3):965-969.
doi:10.1016/j.electacta.2009.09.057 .

Damljanovic, Ivan, Vukicevic, Mirjana, Manojlović, Dragan D., Šojić, Nešo, Buriez, Olivier, Vukicevic, Rastko D., "Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity" in Electrochimica Acta, 55, no. 3 (2010):965-969,
https://doi.org/10.1016/j.electacta.2009.09.057 . .

TY  - JOUR
AU  - Damljanovic, Ivan
AU  - Colovic, Marija
AU  - Vukicevic, Mirjana
AU  - Manojlović, Dragan D.
AU  - Radulović, Niko S.
AU  - Wurst, Klaus
AU  - Laus, Gerhard
AU  - Ratkovic, Zoran
AU  - Joksović, Milan D.
AU  - Vukicevic, Rastko D.
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/618
AB  - New ferrocene derivatives - 1H-1-phenylpyrazole-4-carboxaldehydes containing o-, m- and p- ferrocenylphenyl group at position 3 - were synthesized and characterized. The electrochemical investigation showed that the position of the ferrocenyl group does not affect the redox potential of these compounds. The X-ray crystal structure of the ortho-derivative is also presented. The screening for the in vitro antimicrobial activity against eleven bacterial and three fungal/yeast strains exhibited complete inactivity of these aldehydes, but n-butyl imines of ortho and meta derivatives showed moderate activity compared to those of the used standards. (C) 2009 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Sa, Lausanne
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes
VL  - 694
IS  - 9-10
SP  - 1575
EP  - 1580
DO  - 10.1016/j.jorganchem.2009.01.045
ER  - 

@article{
author = "Damljanovic, Ivan and Colovic, Marija and Vukicevic, Mirjana and Manojlović, Dragan D. and Radulović, Niko S. and Wurst, Klaus and Laus, Gerhard and Ratkovic, Zoran and Joksović, Milan D. and Vukicevic, Rastko D.",
year = "2009",
abstract = "New ferrocene derivatives - 1H-1-phenylpyrazole-4-carboxaldehydes containing o-, m- and p- ferrocenylphenyl group at position 3 - were synthesized and characterized. The electrochemical investigation showed that the position of the ferrocenyl group does not affect the redox potential of these compounds. The X-ray crystal structure of the ortho-derivative is also presented. The screening for the in vitro antimicrobial activity against eleven bacterial and three fungal/yeast strains exhibited complete inactivity of these aldehydes, but n-butyl imines of ortho and meta derivatives showed moderate activity compared to those of the used standards. (C) 2009 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes",
volume = "694",
number = "9-10",
pages = "1575-1580",
doi = "10.1016/j.jorganchem.2009.01.045"
}

Damljanovic, I., Colovic, M., Vukicevic, M., Manojlović, D. D., Radulović, N. S., Wurst, K., Laus, G., Ratkovic, Z., Joksović, M. D.,& Vukicevic, R. D.. (2009). Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes. in Journal of Organometallic Chemistry
Elsevier Science Sa, Lausanne., 694(9-10), 1575-1580.
https://doi.org/10.1016/j.jorganchem.2009.01.045

Damljanovic I, Colovic M, Vukicevic M, Manojlović DD, Radulović NS, Wurst K, Laus G, Ratkovic Z, Joksović MD, Vukicevic RD. Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes. in Journal of Organometallic Chemistry. 2009;694(9-10):1575-1580.
doi:10.1016/j.jorganchem.2009.01.045 .

Damljanovic, Ivan, Colovic, Marija, Vukicevic, Mirjana, Manojlović, Dragan D., Radulović, Niko S., Wurst, Klaus, Laus, Gerhard, Ratkovic, Zoran, Joksović, Milan D., Vukicevic, Rastko D., "Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes" in Journal of Organometallic Chemistry, 694, no. 9-10 (2009):1575-1580,
https://doi.org/10.1016/j.jorganchem.2009.01.045 . .

TY  - JOUR
AU  - Colovic, Marija
AU  - Vukicevic, Mirjana
AU  - Šegan, Dejan M.
AU  - Manojlović, Dragan D.
AU  - Šojić, Nešo
AU  - Somsak, Laszlo
AU  - Vukicevic, Rastko D.
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/909
AB  - Bromination of glycals with tribromides formed in situ from bromine and different bromide salts in dichloromethane (DCM) or acetonitrile (AN) was found to give predominantly the products of anti addition of bromine from the C-6 side in high yields. The same selectivity, which was much higher compared to bromination with bromine alone, was achieved in bromination of these substrates by anodic generation of bromine from the same salts.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Advanced Synthesis and Catalysis
T1  - Electrochemical bromination of peracetylated glycals
VL  - 350
IS  - 1
SP  - 29
EP  - 34
DO  - 10.1002/adsc.200700310
ER  - 

@article{
author = "Colovic, Marija and Vukicevic, Mirjana and Šegan, Dejan M. and Manojlović, Dragan D. and Šojić, Nešo and Somsak, Laszlo and Vukicevic, Rastko D.",
year = "2008",
abstract = "Bromination of glycals with tribromides formed in situ from bromine and different bromide salts in dichloromethane (DCM) or acetonitrile (AN) was found to give predominantly the products of anti addition of bromine from the C-6 side in high yields. The same selectivity, which was much higher compared to bromination with bromine alone, was achieved in bromination of these substrates by anodic generation of bromine from the same salts.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Advanced Synthesis and Catalysis",
title = "Electrochemical bromination of peracetylated glycals",
volume = "350",
number = "1",
pages = "29-34",
doi = "10.1002/adsc.200700310"
}

Colovic, M., Vukicevic, M., Šegan, D. M., Manojlović, D. D., Šojić, N., Somsak, L.,& Vukicevic, R. D.. (2008). Electrochemical bromination of peracetylated glycals. in Advanced Synthesis and Catalysis
Wiley-V C H Verlag Gmbh, Weinheim., 350(1), 29-34.
https://doi.org/10.1002/adsc.200700310

Colovic M, Vukicevic M, Šegan DM, Manojlović DD, Šojić N, Somsak L, Vukicevic RD. Electrochemical bromination of peracetylated glycals. in Advanced Synthesis and Catalysis. 2008;350(1):29-34.
doi:10.1002/adsc.200700310 .

Colovic, Marija, Vukicevic, Mirjana, Šegan, Dejan M., Manojlović, Dragan D., Šojić, Nešo, Somsak, Laszlo, Vukicevic, Rastko D., "Electrochemical bromination of peracetylated glycals" in Advanced Synthesis and Catalysis, 350, no. 1 (2008):29-34,
https://doi.org/10.1002/adsc.200700310 . .