Arylation of sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in ionic liquids

Carlos A. Velázquez; Geoffrey M. Lynn; Vineet Kumar; Larry K. Keefer; Sanjay V. Malhotra

doi:10.1080/00397910903074079

Arylation of sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in ionic liquids

Carlos A. Velázquez, Geoffrey M. Lynn, Vineet Kumar, Larry K. Keefer, Sanjay V. Malhotra

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

2 Scopus citations

Abstract

The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.

Original language	English (US)
Pages (from-to)	1322-1332
Number of pages	11
Journal	Synthetic Communications
Volume	40
Issue number	9
DOIs	https://doi.org/10.1080/00397910903074079
State	Published - Jan 2010
Externally published	Yes

Keywords

Diazeniumdiolate
Ionic liquid
Nitric oxide donor
Nucleophilic displacement

ASJC Scopus subject areas

Organic Chemistry

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10.1080/00397910903074079

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title = "Arylation of sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in ionic liquids",

abstract = "The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.",

keywords = "Diazeniumdiolate, Ionic liquid, Nitric oxide donor, Nucleophilic displacement",

author = "Vel{\'a}zquez, {Carlos A.} and Lynn, {Geoffrey M.} and Vineet Kumar and Keefer, {Larry K.} and Malhotra, {Sanjay V.}",

note = "Funding Information: This work was supported by federal funds from the National Cancer Institute, National Institutes of Health (NIH) under contract HHSN261200800001E with SAIC–Frederick Inc. as well as by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.",

year = "2010",

month = jan,

doi = "10.1080/00397910903074079",

language = "English (US)",

volume = "40",

pages = "1322--1332",

journal = "Synthetic Communications",

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T1 - Arylation of sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in ionic liquids

AU - Velázquez, Carlos A.

AU - Lynn, Geoffrey M.

AU - Kumar, Vineet

AU - Keefer, Larry K.

AU - Malhotra, Sanjay V.

N1 - Funding Information: This work was supported by federal funds from the National Cancer Institute, National Institutes of Health (NIH) under contract HHSN261200800001E with SAIC–Frederick Inc. as well as by the Intramural Research Program of the NIH, National Cancer Institute, Center for Cancer Research.

PY - 2010/1

Y1 - 2010/1

N2 - The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.

AB - The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.

KW - Diazeniumdiolate

KW - Ionic liquid

KW - Nitric oxide donor

KW - Nucleophilic displacement

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Arylation of sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in ionic liquids

Abstract

Keywords

ASJC Scopus subject areas

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