A low-temperature ammonium ylid rearrangement: enhanced reactivity engendered by rigiditySancon, J. and Sweeney, J.B. (2008) A low-temperature ammonium ylid rearrangement: enhanced reactivity engendered by rigidity. Synlett (14). pp. 2213-2214. ISSN 0936-5214 Full text not archived in this repository. It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1055/s-2008-1078256 Abstract/SummarySigmatropic rearrangement of tetrahydropyridine-derived ammonium is a valuable method for the preparation of substituted prolines. These reaction normally require elevated temperatures to proceed, but bicyclic tetrahydropyridine-like ylid I undergoes rearrangement at -15 degrees C; the extra rigidity of the azabicyclo[3.3.0]octene system preorganizes the transition state and lowers the activation energy for rearrangement.
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