Tetrahedron

X= Y-ZH systems as potential 1, 3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1, 3-azaprotio …

…, J Markandu, T Perrior, S Surendrakumar, WJ Warnock

文献索引：Grigg, Ronald; Markandu, Jasothara; Perrior, Trevor; Surendrakumar, Sivagnanasundram; Warnock, William J. Tetrahedron, 1992 , vol. 48, # 33 p. 6929 - 6952

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被引用次数: 116

摘要

Aldoximes and ketoximes possessing γ-or δ-alkenyl substituents undergo thermal conversion to 5-and 6-membered cyclic nitrones via a 1, 3-azaprotio cyclotransfer, a 2n+ 2σ+ 2π concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state ...