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http://dx.doi.org/10.5012/jkcs.2009.53.3.302

Azomethine Yilde Forming Photoreaction of N-(Tributylstannyl)methylphthalimide  

Jeong, Ho-Cheol (Department of Chemistry, Pusan National University)
Park, Ki-Hyun (Department of Cheamistry, Pusan National University)
Park, Hea-Jung (Department of Cheamistry, Pusan National University)
Cho, Dae-Won (Department of Cheamistry, Pusan National University)
Yoon, Ung-Chan (Department of Cheamistry, Pusan National University)
Publication Information
Journal of the Korean Chemical Society / v.53, no.3, 2009 , pp. 302-307 More about this Journal
Abstract
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 $D_2O-CH_3$CN 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.
Keywords
N-(tributylstaanyl)methylphthalimide; Azomethine ylide; Photochemical reaction; Mono-deuterated N-methylphthalimide;
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