- Reactions with Betaines, XXIV: Reactions of Trimethylammonium Acetic Acid Betaine with Reactive Halides
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Diethyl bromomalonate and bromoacetonitrile, respectively, react with trimethylammonium acetic acid betaine in ethanol to give diethyl tartronate and glycolic acid nitrile, respectively.By analogy, ethyl α-chloroacetonate and ethyl bromopyruvate yield the respective hydroxy derivatives which were identified by their osazones 2 and 3.Under the same experimental conditions, mesoxalic acid and its dimethyl ester, respectively, are formed from dibromo malonic acid and its dimethyl ester and were characterized by their known hydrazones 8 and 9. - Keywords: Trimethylammonium acetic acid betaine; Diethyl tartronate; 1-Carbethoxy-2-methyl-(2,4-dinitrophenyl) osazone; 1-Carbetoxy-(2,4-dinitrophenyl) osazone; Glycolic acid nitrile.
- Ziegler, Erich,Wittmann, Helga,Sterk, Heinz
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p. 907 - 912
(2007/10/02)
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- Reactions with Betaines, XXIII. Reactions of Nitrogen- and Sulphur-Betaines with Reactive Halides
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Trimethylammonium acetic betain (1) reacts with phenacyl bromide and ethyl bromoacetate, respectively, to give the ester bromides 2 and 7.These can be hydrolyzed with aqueous sodium hydrogencarbonate at 20 deg C to yield besides 1 both C-benzoyl-methanol (3) and the glycolic acid ester 8, respectively.The reaction can also be performed in one step by reacting the betain (1) (with can act as a base) in a double molar ratio with the active halide. - Keywords: Trimethylammonium acetic acid betain; Trimethylammonium acetic acid phenacyl ester bromide; Trimethylammonium acetic acid acetoxy ethyl ester bromide; Phenacyl alcohol; Ethyl glycolate
- Wittmann, Helga,Ziegler, Erich
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p. 103 - 112
(2007/10/02)
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