Studies on the [2,3]-Stevens rearrangement of aziridinium ions |
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Authors: | Gareth J Rowlands William Kentish Barnes |
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Institution: | Department of Chemistry, University of Sussex, Falmer, Brighton BN1 9QJ, UK |
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Abstract: | The aziridinium ylide generated by the intramolecular reaction of a metal carbenoid tethered to a vinylaziridine undergoes 2,3]-Stevens rearrangement to furnish the indolizidine skeleton. It is essential that the correct nitrogen invertomer is used or a competing 1,5]-hydrogen shift predominates. During the preparation of a second system a `one-pot' acylation-3,3]-Claisen rearrangement was observed, delivering a seven-membered lactam. |
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Keywords: | Vinylaziridine Aziridinium Ylide Carbene [2 3]-Stevens rearrangement |
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