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Unexpected cycloadducts from 1,3-dipolar cycloaddition of 3,4-dehydromorpholineN-oxide toN-cinnamoyl piperidines—first report of the novel formation of 2:1 cycloadducts

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
46
Issue
15
Identifiers
DOI: 10.1016/j.tetlet.2005.02.083
Keywords
  • Nitrone
  • Dipolar Cycloaddition
  • Intermolecular
  • Isoxazolooxazines

Abstract

Abstract A series of unexpected cycloadducts along with normal cycloadducts have been isolated from the 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to piperidides of cinnamic acid and para-substituted cinnamic acids and these were analyzed by X-ray crystallography to reveal novel solid-state structures. At first, 1:1 cycloadducts were formed which underwent in situ nucleophilic attack by another reduced nitrone moiety. A plausible iminium–oxonium ion mechanism has been proposed.

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