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KMID : 1059520090530030302
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Journal of the Korean Chemical Society
2009 Volume.53 No. 3 p.302 ~ p.307
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Azomethine Yilde Forming Photoreaction of N-(Tributylstannyl)methylphthalimide
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Jeong Ho-Cheol
Park Ki-Hyun
Park Hea-Jung
Cho Dae-Won
Yoon Ung-Chan
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Abstract
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Investigation was conducted to examine whether photochemical reaction of N-(tributylstannyl)- methylphthalimide generates an azomethine ylide intermediate in its excited state as its silyl derivative N-(trimethylsilyl)methylphthalimide which has been observed to form an azomethine ylide. The irradiation of N-(tributylstannyl)methylphthalimide in D2O-CH3CN generates mono-deuterated N-methylphthalimide as an exclusive product which supports the efficient generation of azomethine ylide intermediate and its trapping by water molecule through a proto-destannylation pathway. However the generated tributylstannyl subsitiuted ylide was not observed to be trapped with a dipolarophile such as methyl acrylate and acrylonitrile present in the reactions which is in contrast with the ylide from N-(trimethylsilyl)methylphthalimide.
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KEYWORD
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N-(tributylstaanyl)methylphthalimide, Azomethine ylide, Photochemical reaction, Mono-deuterated N-methylphthalimide
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