Sultone chemistry

Roberts, David W.; Williams, D. L.

doi:10.1016/s0040-4020(01)90041-9

Cited by 117 publications

(45 citation statements)

References 94 publications

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“…However, N-alkylation using even this strong alkylating reagent required 7 days to afford 34% conversion to product. Finally, the reagent 1,3-propane sultone is widely used in industry to introduce the waterÁsoluble, three-carbon sulfobetaine moiety in a variety of molecules and polymers [9]. Our results with acridan N-alkylation reactions suggest that sodium 3-bromopropane sulfonate in ILs may be a benign alternative to 1,3-propane sultone for such applications.…”

Section: Resultsmentioning

confidence: 75%

“…For comparison, KamletTaft parameter p* of water is 1.09 [19]. In our earlier study [9], we noted excellent correlation between the parameter p* of the solvent and the extent of conversion to N-sulfopropyl acridinium ester product in the reaction of its acridine ester precursor with limited quantities of propane sultone. However, the alkylation reaction was not particularly sensitive to either the acidity of the cation or the basicity of the anion comprising the IL as reflected by the KamletTaft parameters a and b, respectively.…”

Section: Introductionmentioning

confidence: 92%

“…The formation of polysulfonated acridinium ester by-products also complicates chromatographic purification and lowers the yield of the N-sulfopropyl acridinium dimethylphenyl ester product [1]. Despite its toxicity, 1,3-propane sultone is widely used to introduce a three-carbon sulfobetaine in various dyes and polymers to increase their water solubility [9]. We wanted to develop less toxic alternatives to this reagent for introducing the Nsulfopropyl group in chemiluminescent acridinium esters.…”

Section: Introductionmentioning

confidence: 99%

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A green synthesis of chemiluminescent N-sulfopropyl acridinium esters in ionic liquids without using the carcinogen 1,3-propane sultone

Natrajan

Wen

2013

Green Chemistry Letters and Reviews

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Chemiluminescent acridinium dimethylphenyl esters containing hydrophilic N-sulfopropyl groups in the acridinium ring are used as labels in automated immunoassays for clinical diagnostics. Introduction of the N-sulfopropyl group in these labels is normally accomplished by N-alkylation of the corresponding, nonchemiluminescent acridine ester precursors with the toxic carcinogen 1,3-propane sultone. In the current study, we report that sodium 3-bromopropane sulfonate in ionic liquids (ILs) is a benign alternative to 1,3-propane sultone for introducing the N-sulfopropyl group in chemiluminescent acridinium ester labels. The sultone reagent can be eliminated in the synthesis of N-sulfopropyl acridinium dimethylphenyl ester labels by taking advantage of the increased reactivity of acridan esters toward nontoxic sodium 3-bromopropane sulfonate in [BMIM] [BF 4 ]. Sodium 3-bromopropane sulfonate in ILs is also potentially a nontoxic alternative to 1,3-propane sultone for introducing the water-soluble, three-carbon sulfobetaine moiety in other molecules as well.

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Section: Resultsmentioning

confidence: 75%

Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A green synthesis of chemiluminescent N-sulfopropyl acridinium esters in ionic liquids without using the carcinogen 1,3-propane sultone

Natrajan

Wen

2013

Green Chemistry Letters and Reviews

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“…In their reaction with nucleophiles, the nitrogen centres were quaternized resulting in zwitterionic centres along the polymeric chain (Scheme 1). The sulfopropyl groups are introduced by reaction of nucleophiles with commercially available 1,3-propane sultone [20]. The sulfopropyl group has been used extensively to improve the hydrophilicity of a variety of surfactants, dyes, nucleosides, proteins and polymers [21][22][23][24][25][26].…”

Section: Resultsmentioning

confidence: 99%

Surface Photografting of Novel Sulfobetaine Copolymers on Silica

Kumar¹,

Tarannum²,

Singh³

2012

MSA

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A couple of novel sulfobetaine copolymer is developed via Michael-type addition reaction. The comonomers, diamines and maleimide react via Michael reaction through UV irradiation using AIBN as photoinitiator producing polyamine chain. Further, sulfobetaine copolymers were obtained on treatment of the polyamine with sulfopropylating agent, 1,3-propane sultone. These novel sulfobetaine polymers were grafted on silica surface to produce responsive biocompatible surface. This easy straightforward, catalyst free facile protocol for synthesis of polymer grafted surface is useful for developing biomedical devices. Additionally, both the copolymers show fluorescence characteristics.

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“…In our studies of the rearrangement reactions of 1-methoxy-2,6-dimethylbenzobarrelene derivatives in sulfuric acid we obtained the sultone (1) whose structure was established by X-ray diffraction (Brown, Heaney & Mason, 1984). The product was thought to arise by sulfonation of an olefin (Roberts & Williams, 1987) concurrently with a 1,2-acyl shift. Since the complex formed between dioxan and sulfur trioxide is known to have electrophilic properties (Wolinsky, Dimmel & Gibson, 1967;Dimmel & Fu, 0108-2701/87/091800-03501.50 1973) we have studied the reaction of the ketone (2) with that reagent.…”

mentioning

confidence: 99%