Molecules 2009, 14(2), 777-784; doi:10.3390/molecules14020777
Article

Methyl Carbonium Ion Migration during the Reaction of 4-Chloro-5-methoxyl-3(2H)-pyridazinone with Trifluoroethylation Agents

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Received: 20 November 2008; in revised form: 18 December 2008 / Accepted: 4 January 2009 / Published: 13 February 2009
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: To synthesize 4-chloro-5-methoxy-2-(b-trifluoroethyl)-3(2H)-pyridazinone (4), the reactions of 4-chloro-5-methoxy-3(2H)-pyridazinone (5) with RCH2CF3 (R = I, TsO, MsO, TfO) in different solvents were studied. It was found that methyl group migration took place during this reaction. An oxonium salt 9 was suggested as the active intermediate for the formation of the byproduct4-chloro-5-methoxy-2-methyl-3(2H)-pyridazinone (7) and 4-chloro-2-methyl-5-(b-trifluoroethoxy)-3(2)-pyridazinone(8).
Keywords: 4; 5-Dichloro-3(2H)-pyridazinone; 4-Chloro-5-methoxy-3(2H)-pyridazinone; -Trifluoroethylation; Oxonium; Methyl group migration; Alkylation
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MDPI and ACS Style

Li, Q.; Lin, G.; Liu, L.; Yang, Z.; Zhang, L.-H. Methyl Carbonium Ion Migration during the Reaction of 4-Chloro-5-methoxyl-3(2H)-pyridazinone with Trifluoroethylation Agents. Molecules 2009, 14, 777-784.

AMA Style

Li Q, Lin G, Liu L, Yang Z, Zhang L-H. Methyl Carbonium Ion Migration during the Reaction of 4-Chloro-5-methoxyl-3(2H)-pyridazinone with Trifluoroethylation Agents. Molecules. 2009; 14(2):777-784.

Chicago/Turabian Style

Li, Qin; Lin, Guichun; Liu, Li; Yang, Zhenjun; Zhang, Li-He. 2009. "Methyl Carbonium Ion Migration during the Reaction of 4-Chloro-5-methoxyl-3(2H)-pyridazinone with Trifluoroethylation Agents." Molecules 14, no. 2: 777-784.

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