• Bulletin of the Korean Chemical Society
• /
• 제18권12호
• /
• pp.1288-1291
• /
• 1997

4-Allylanisole was polymerized with AlCl3 as a catalyst. The polymerization was carried out in nitroethane at various temperatures with changing the ratio of the initiator to the monomer concentration. The weight averge molecular weights measured by gel permeation chromatography in chloroform with polystyrene standards were between 1,500 and 4,700. 1H NMR spectroscopy showed that the polymerization proceeded through a stepwise aromatic electrophilic substitution reaction along with a minor chain-reaction, resulting in a branched polymer. 4-Chloromethylanisole was also polymerized with AlCl3 in nitroethane through an aromatic electrophilic substitution reaction to give a high molecular weight polymer (Mw=88,000).

• 한국자기공명학회논문지
• /
• 제22권4호
• /
• pp.115-118
• /
• 2018

Dipyrromethane 2 functionalized with 3-chloropropyl group on the meso carbon undergoes an unusual intramolecular electrophilic aromatic substitution reaction in the presence of $NaN_3$ instead of a simple nucleophilic substitution reaction. As a result, a new chiral dipyrromethane 1 was synthesized. In this reaction, the ${\beta}$-carbon of the pyrrole ring functions as a nucleophile while the carbon next to the chlorine atom acts as an electrophile. Interestingly, this reaction progresses even in the absence of an acid catalyst. Compound 1 was fully characterized by $^1H-^1H$ and $^1H-^{13}C$ COSY NMR spectroscopic analyses and the high resolution EI mass spectrometry.

• 대한화학회지
• /
• 제19권3호
• /
• pp.179-185
• /
• 1975

방향족 치환반응을 모형과하여 유사분자 착물이 천이상태가 될수있음을 단수 Huckel법으로 증명하고 새로운 방향족 치환반응의 기구를 제안하였다. 아울러 이 유사분자 착물을 양자역학적 선동법을 이용하여 안정화 에너지식을 유도하고 많은 탄소화합물의 안정화 에너지식을 유도하고 많은 탄소화합물의 안정화 에너지를 구하였다. 이 안정화 에너지로 어떤 방향족 화합물이 유사분자 착물을 형성하는 위치와 그 화합물의 치환반응의 결합 시약이 방향족 화합물에 부가반응이 일어나는 반응에까지 널리 설명할 수 있는 이점이 있다.

• Bulletin of the Korean Chemical Society
• /
• 제31권7호
• /
• pp.1837-1838
• /
• 2010

• Bulletin of the Korean Chemical Society
• /
• 제23권9호
• /
• pp.1208-1254
• /
• 2002

Photoreaction of N-(o-halophenyl)acetamide in basic acetonitrile produces an intramolecular substituted product, 2-methylbenzoxazole in addition to reduced product, acetanilide, whereas photoreaction of N-(o-halobenzyl) acetamide affords a reduced product, N-benzylacetamide only. On the basis of preparative reaction, kinetics, and UV/vis absorption behavior, an electrophilic aromatic substitution of aryl halide with oxygen of its amide bond are proposed.

• Bulletin of the Korean Chemical Society
• /
• 제24권8호
• /
• pp.1181-1187
• /
• 2003

Condensation of 4-cyano-5,6-dimethyl-3-pyridazinone 1 with aromatic aldehydes gave the novel styryl derivatives 2a-c. Refluxing of compound 2a with phosphorus oxychloride furnished 3-chloropyridazine derivative 3. Compound 3 was reacted with thiourea and produced pyridazine-3(2H)thione 4. Thieno[2,3-c]- pyridazines 5a-e were achieved by cycloalkylation of compound 4 with halocompounds in methanol under reflux and in the presence of sodium methoxide. Also, refluxing of compound 4 with N-substituted chloroacetamide in the presence of potassium carbonate afforded thienopyridazines 6a-e. Cyclization of compound 6 with some electrophilic reagents as carbon disulfide and triethyl orthoformate furnished the novel pyrimido[4',5':4,5]thieno[2,3-c]pyridazines 12 and 13a-c, respectively. Diazotisation of compound 6 with sodium nitrite in acetic acid produced the pyridazino[4',3':4,5]thieno[3,2-d][1,2,3]triazines 14a-c. Ternary condensation of compound 1, aromatic aldehydes and malononitrile in ethanol containing piperidine under reflux afforded the novel phthalazines 16a-c. Compound 3 was subjected to some nucleophilic substitution reactions with amines and sodium azide and formed the aminopyridazines 17a, b and tetrazolo[1,5-b]-pyridazine 19, respectively. The structures of the synthesized compounds were established by elemental and spectral analyses.