The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions

Reihaneh Salmasi; Mostafa Gholizadeh; Alireza Salimi; Jered C. Garrison

doi:10.1007/s13738-016-0919-6

The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions

Reihaneh Salmasi, Mostafa Gholizadeh, Alireza Salimi, Jered C. Garrison

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH₂–CH₂– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]

Original language	English (US)
Pages (from-to)	2019-2028
Number of pages	10
Journal	Journal of the Iranian Chemical Society
Volume	13
Issue number	11
DOIs	https://doi.org/10.1007/s13738-016-0919-6
State	Published - Nov 1 2016

Keywords

Bromination
Crystal structure
Nucleophilic substitutions
Regioselectivity
Solvent-free

ASJC Scopus subject areas

Chemistry(all)

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10.1007/s13738-016-0919-6

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The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions. / Salmasi, Reihaneh; Gholizadeh, Mostafa; Salimi, Alireza et al.

In: Journal of the Iranian Chemical Society, Vol. 13, No. 11, 01.11.2016, p. 2019-2028.

Research output: Contribution to journal › Article › peer-review

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title = "The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions",

abstract = "Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]",

keywords = "Bromination, Crystal structure, Nucleophilic substitutions, Regioselectivity, Solvent-free",

author = "Reihaneh Salmasi and Mostafa Gholizadeh and Alireza Salimi and Garrison, {Jered C.}",

note = "Funding Information: The authors are grateful to the Ferdowsi University of Mashhad Research Council for the financial support of the project Code Number 36987. Publisher Copyright: {\textcopyright} 2016, Iranian Chemical Society.",

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T1 - The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions

AU - Salmasi, Reihaneh

AU - Gholizadeh, Mostafa

AU - Salimi, Alireza

AU - Garrison, Jered C.

N1 - Funding Information: The authors are grateful to the Ferdowsi University of Mashhad Research Council for the financial support of the project Code Number 36987. Publisher Copyright: © 2016, Iranian Chemical Society.

PY - 2016/11/1

Y1 - 2016/11/1

N2 - Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]

AB - Abstract: 1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion. Graphical Abstract: [Figure not available: see fulltext.]

KW - Bromination

KW - Crystal structure

KW - Nucleophilic substitutions

KW - Regioselectivity

KW - Solvent-free

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The synthesis of 1,2-ethanediylbis(triphenylphosphonium) ditribromide as a new brominating agent in the presence of solvents and under solvent-free conditions

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