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Communication | Special issue | Vol 84, No. 1, 2012, pp.393-400
Published online, 27th September, 2011
DOI: 10.3987/COM-11-S(P)86
[3+2] Cycloaddition of Seleno- and Thioaldehydes with Cyclic Azomethine Imines

Hajime Maeda, Yusuke Takamizawa, and Masahito Segi*

*Chemistry Course, College of Science and Engineering, School of Chemistry, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan


Reaction of seleno- and thioaldehydes with cyclic azomethine imines in refluxing toluene gave [3+2] cycloadducts as a diastereomeric pure form in high yields. Thermal cycloreversion of the [3+2] cycloadducts regioselectively occurred to regenerate seleno- and thioaldehydes which can be trapped in situ by 2,3-dimethyl-1,3-butadiene.