Abstract
Short-lived γ-halocarbanions can be trapped by active electrophiles such as aldehydes, imines, and Michael acceptors to give anionic adducts, which undergo intramolecular substitution to give substituted tetrahydrofurans, pyrrolidines, and cyclopentanes. This has underlain a new method for the synthesis of these valuable ring systems. We have determined the acidity of the γ-halocarbanion precursors and have shown that the halogen atoms in the γ-position relative to the carbanion center exert a significant stabilizing effect on the carbanion.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1771–1783, September, 2004.
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Barbasiewicz, M., Judka, M. & Makosza, M. New reactions of γ-halocarbanions: underestimated reactive intermediates in organic synthesis. Russ Chem Bull 53, 1846–1858 (2004). https://doi.org/10.1007/s11172-005-0043-8
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DOI: https://doi.org/10.1007/s11172-005-0043-8