88237-05-2Relevant academic research and scientific papers
Studies on Ketene and Its Derivatives. CXIII. Reaction of Dichloroketene with Aromatic Amine N-Oxides
Katagiri, Nobuya,Niwa, Ryuji,Furuya, Yoichi,Kato, Tetsuzo
, p. 1833 - 1841 (2007/10/02)
Reaction of dichloroketene with pyridine 1-oxide (1) gave four products, namely, 2-dichloromethylpyridine (2), 4-dichloromethylpyridine (3), 3,3,7-trichloro-6-dichloroacetyl-2-oxo-2,3,3a,6,7,7a-hexahydrofuropyridine (4), and 3,3-dichloro-6-dichloroacetyl-7-hydroxy-2-oxo-2,3,3a,6,7,7a-hexahydrofuropyridine (5).Reaction of dichloroketene with 1, followed by treatment with abs. methanol gave 3, methyl 2,2-dichloro-2-(2-pyridyl)acetate (6), and methyl 2,2-dichloro-2-(4-pyridyl)acetate (7).Similar reaction of dichloroketene with methylpyridine 1-oxides gave the corresponding 2-dichloro and 4-dichloro methylpyridines.On the other hand, reaction of dichloroketene with 2,6-dimethylpyridine 1-oxide (18), followed by treatment with abs. methanol gave 4-dichloromethyl-2,6-dimethylpyridine (19) and bis(2,6-dimethyl-4-pyridyl)dichloromethane (21).Dichloroketene also reacted with quinoline 1-oxide (24) and isoquinoline 2-oxide (29) to give the corresponding dichloromethyl derivatives (25 and 26, and 30, respectively).Keywords --- aromatic amine N-oxide; dichloroketene; dichloromethylpyridine; dichloromethylquinoline; dichloromethylisoquinoline
