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"디아조화된 5 -Amino - 3 , 4 - Dimethylisoxazole의 아조 - 커플링 및 分子內 고리화 反應"
梁一友 陸軍士官學校 1983 한국군사학논집 Vol.25 No.-
Azo-coupling and intramolecular cyclization reactions of diazotized 5-amino-3, 4-dimethylisoxazole were examined in nonpolar solvent. 5-Amino-3, 4-dimethyelisoxazole was diazotized in a mixed solvent(consist of methylene chloride and ether) by employing boron trifluoride and t-butylnitrite. The resulting diazonium tetrafluoride coupled with N, N-dimethylaniline and the coupling product could be isolated by means of copper(Ⅱ) complex. The ortho-alkyl heteroaromatic diazonium salt gave cyclized product in phase transfer catalytic(PTC) reaction conditions using 18-crown-6 as a PTC catalyst. The structures of products were confirmed by their ir, pmr, mass spectra, and results of the elemental analysis.
Bis-IBA 유도체의 합성 및 신경작용제 가수분해 촉매 효과 연구
양일우,강덕구 한국군사과학기술학회 1999 한국군사과학기술학회지 Vol.2 No.1
Four bis-iodosobenzoic acid derivatives have been synthesizd in 5 steps following literature methods from 5-hydroxyantranilic acid; 1) diazotization and iodination, 2) acid protection, 3) tosylate substitution, 4) acid deprotection, 5) oxidation of iodo-substituent to iodoso group. Catalytic effects of new 5,5'-tri-, tetra-, deca-, polyethyleneglycoxy- bis(2-iodosobenzoic acid) on hydrolysis reactions of PNPDPP(p-nitrophenyl diphenyl phosphate), sarin and soman have been measured to determine the role of ethyleneglycoxy substituents as phase transfer catalysts. At $25{\pm}0.2^{\circ}C$, pH 8.0, and cetyltrimethyl ammonium chloride(CTACl) micelle solution condition, bis-IBA derivatives hydrolyzes PNPDPP with maximum pseudo-first order rate constant($K_{obsd}^{max}$) of 0.32035 ~ 0.13659 $sec^{-1}$, which corresponds to 2~18 times rate increase than those of unsubstituted o-IBA[iodosobenzoate($K_{obsd}^{max}=0.0645sec^{-1}$), iodoxybenzoate (<tEX>$K_{obsd}^{max}$ = $0.0178 sec^{-1}$)]. At the similar condition for PNPDPP hydrolysis, bis-IBA derivatives also act as efficient catalysts for hydrolytic cleavage of nerve agents such as sarin and soman. Hydrolysis rate constant with 5,5'-polyethyleneglycoxy- bis(2-iodosobenzoic acid) shows 7 times increase than that of simple 5-hydroxy-2-iodosobenzoic acid.
크라운에테르 유기산을 이용한 알칼리 금속이온의 경쟁 용매 추출에서의 협력 및 이온강도 효과
양일우,정영진 陸軍士官學校 1991 한국군사학논집 Vol.40 No.-
The size-selective synergism and ionic strength effects in competitive solvent extraction of alkali metal cations from water to chloroform using crown other compounds were investigated. The synergistic factor of neotridecanoic acit(NTDA) and monobenzo-18-crown-6 mixture, which compounds were selected for our purpose, was ca 10 with apparent size selectivity. The selectivity coefficient of the synergistic mixture calculated for K^+/Rb^+ was 1.6. The result was compared with a monobenzo-18-crown-6 cerivative(4), which contains a decanoic acid moiety as a functionalized pendant group. Maximum metal loading in the functionalized crown compound was twice of those obtained in the synergistic system. Effect of ionic strength in competitive solvent extraction was determined using2-(sym-dibenzo-16-crown-5-oxy) hexanoic acid. By decreasing ionic strength of the aqueous medium from 1.25M to 0.05M, two general trends were observed. One was the decrease in overall metal loading and the other was decrease in selectivity. Both these phenomena seem to be caused mainly by the significant decrease in the concentration of the most extractable ion, Na^+ in this system, while concentrations of the other ions remain virtually constant in the organic phase.
양일우,김정수 陸軍士官學校 2000 한국군사학논집 Vol.56 No.-
Two new iodosobenzoic acids(IBA) such as 5-[N-(n-dodecyl)-N, N-dimethyl-N(β-ethyloxy) ammonium]-2-IBA and 5-[N-(n-dodecyl)-N, N-dimethyl-N(β-ethyloxy) ammonium]-2-IBA were synthesized and their cataytic effects on hydrolysis reactions of p-nitrophenyldiphenylphosphate(PNPDPP), sarin(GB) and soman(GD) were determined. 5-[N-(n-dodecyl)-N, N-dimethyl-N(β-ethyloxy) ammonium]-2-IBA and 5-[N-(n-dodecyl)-N, N-dimethyl-N(β-ethyloxy) ammonium]-2-IBA effectively catalyzed hydrolytic cleavage of PNPDPP. In kinetic studies of hydrolysis reaction using 5-[N-(n-hexadecy)-N, N-demethyl-N-(β-ethyloxy) ammonium]-2-IBA as a catalyst, it was shown that PNPDPP was cleaved with k_∅^max≥ 0.7965 sec^-1 which is 12~45 times more reactive than iodosobenzoate (k_∅^max=0.0645 sec^-1) or iodoxybenzoate (k_∅^max=0.0178 sec^-1) in aqueous cetyltrimethylammonium chloride(CTACl) micellar solution at 25±0.2℃ and pH 8.0 5-[N-(n-dodecyl)-N, N-dimethyl-N(β-ethyloxy) ammonium]-2-IBA and 5-[N-(n-dodecyl)-N, N-dimethyl-N(β-ethyloxy) ammonium]-2-IBA also catalyzed hydrolytic cleavage of GB and GD The latter catalyst showed enhenced reacticity by 5.6(GD) ~ 7.8(GB) time compared to 5-hydoxy-2-IBA in aqueous CTACl micellar solution at 25±0.2℃ and pH 8.0 haning both hydrophiclic and lipophilic characters in the molecules, new reagents appeared to be superior to the simple iodosobenzoic acid, iodosobenzoate and iodoxybenzoate in catalitic hydorolysis of PNPDPP, GB and GD.