SYNTHESIS AND HYDROLYTIC STABILITY OF<i>TERT</i>-BUTOXYDIMETHYLSILYL ENOL ETHERS

Fataftah, Zacharia A.; Rawashdeh, Abdel‐Monem M.; Sotiriou-Leventis, Lia

doi:10.1081/scc-100104840

Cited by 3 publications

(1 citation statement)

References 13 publications

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“…Apparently, TBS-luminol converts to unprotected luminol with a considerable rate, presumably by Si-O bond cleavage in the presence of base; in fact, it is known that TBS protection of enol groups is rather labile under basic conditions. 39 To obtain high sensitivity, background signal should be minimized. However, unfortunately basic conditions cannot be avoided, since the type and amount of base play a crucial role in the luminol CL process, having a strong inuence on the kinetics of the monoanion generation, and the formation of hydroxyl radicals and superoxide anions.…”

Section: Resultsmentioning

confidence: 99%

Design principles of chemiluminescence (CL) chemodosimeter for self-signaling detection: luminol protective approach

et al. 2014

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Chemiluminescence (CL) sensors can provide convenience and high sensitivity because they do not require an external excitation light source to produce a fluorescence signal. However, most CL based detection systems do not have a built-in self-signaling process, leading to inefficient and complex protocols due to the required multistep cascade reactions. Here, we develop a CL based sensory system with a built-in self-signaling feature by adapting the chemodosimeter concept. We found that a masking group incorporated to luminol efficiently suppresses the CL of luminol and that selective removal of the masking group by a target analyte can turn on the CL process, generating a sensitive fluorescence turnon signal. Through systematic studies on newly devised TBS-luminol and TIPS-luminol, we optimized the molecular design parameters to achieve a highly sensitive and selective CL chemodosimeter. The optimized conditions rendered highly sensitive (Limit of Detection (LOD) ¼ 18 nM) and selective fluoride sensing in aqueous environments. We anticipate that our new sensor system offers an efficient way to achieve highly sensitive, selective, and convenient CL turn-on detection of various important analytes.

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Section: Resultsmentioning

confidence: 99%

Design principles of chemiluminescence (CL) chemodosimeter for self-signaling detection: luminol protective approach

et al. 2014

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ChemInform Abstract: Synthesis and Hydrolytic Stability of tert‐Butoxydimethylsilyl Enol Ethers.

2001

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Synthesis and Hydrolytic Stability of tert-Butoxydimethylsilyl EnolEthers.-Several tert-butoxydimethylsilyl enol ethers are synthesized for the first time in good to excellent yields by reaction of Cl-SiMe 2 -O-tBu with corresponding aldehydes and ketones. In general, the stereoselectivity of the reaction is influenced by the method of enol ether formation (thermodynamic vs. kinetic). As expected, kinetic control favors the formation of (E)-enolates. The hydrolytic stability of the silyl enol ethers obtained is superior to trimethylsilyl and comparable to tert-butyldimethylsilyl and (2,4,6-tri-tertbutylphenoxy)diphenylsilyl enol ethers.-(FATAFTAH, ZACHARIA A.; RAWASHDEH, ABDEL-MONEM M.; SOTIRIOU-LEVENTIS, CHARIKLIA; Synth. Commun. 31 (2001) 15, 2379-2389; Dep. Chem., Yarmouk Univ., Irbid, Jordan; EN)

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Synthesis of a Particular Class of Silicon‐Tethered Dinucleophiles: Several Propargyloxydimethylsilyl Enol Ethers

Fataftah¹,

Sawalhah²,

Rawashdeh³

2006

Synthetic Communications

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The propargyloxydimethylsilyl enol ethers derived from propanone, 2-butanone, 3,3-dimethyl-2-butanone, 3-pentanone, 4-methyl-2-pentanone, 2-heptanone, 4-heptanone, 2,6-dimethyl-4-heptanone, cyclopentanone, cyclohexanone, cycloheptanone, benzophenone, and propiophenone have been synthesized by two methods: The thermodynamic method is conducted by heating the propargyloxysilyl chloride, triethylamine, and the corresponding ketone in acetonitrile at 40-508C for less than an hour in the presence of an equimolar amount of sodium iodide; the mixture is maintained at that temperature for an hour. The yields were in the range of 50-95%. In method two (kinetic controlled), lithium diisopropylamide (LDA) was used as a base to abstract the acidic hydrogen, and then the resulted enolate was quenched with silyl chloride, with lower yields than the previous method. NMR, IR, and elemental analysis were used to characterize the products. Some reactions of these compounds have been investigated.

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SYNTHESIS AND HYDROLYTIC STABILITY OFTERT-BUTOXYDIMETHYLSILYL ENOL ETHERS

Cited by 3 publications

References 13 publications

Design principles of chemiluminescence (CL) chemodosimeter for self-signaling detection: luminol protective approach

Design principles of chemiluminescence (CL) chemodosimeter for self-signaling detection: luminol protective approach

ChemInform Abstract: Synthesis and Hydrolytic Stability of tert‐Butoxydimethylsilyl Enol Ethers.

Synthesis of a Particular Class of Silicon‐Tethered Dinucleophiles: Several Propargyloxydimethylsilyl Enol Ethers

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