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  • Title: Microwave- and photoirradiation-induced staudinger reactions of cyclic imines and ketenes generated from alpha-diazoketones. A further investigation into the stereochemical process.
    Author: Liang Y, Jiao L, Zhang S, Xu J.
    Journal: J Org Chem; 2005 Jan 07; 70(1):334-7. PubMed ID: 15624943.
    Abstract:
    Reactions of ketenes generated from alpha-diazoketones with a series of acyclic and cyclic imines were investigated under both microwave and photoirradiation conditions. The results indicate that the zwitterionic azabutadiene-type intermediates yielded from imines and ketenes undergo a conrotatory ring closure exclusively to produce beta-lactams. It is notable that no Woodward-Hoffmann product was found under the ultraviolet irradiation. The photoirradiation-induced Staudinger reaction shows a different stereoselectivity from the electrocyclic reaction of substituted 1,3-butadiene.
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