cheminform abstract: ring-retentive deprotonation of cyclopropene-3-carboxamides
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Cyclopropane derivativesQ 0021 DOI: 10.1002/chin.201045053
Ring-Retentive Deprotonation of Cyclopropene-3-carboxamides. — The anionic species generated from the title cyclopropenes exhibit a remarkable stability towards ring opening, even at elevated temperatures. The reaction of these species with a variety of electrophiles affords the corresponding 1-substituted cyclopropenes, except for the reaction with allyl iodide. In the latter case, a rapid ring opening occurs affording (di-allylpropargyl)carboxamides. In contrast, allyl bromide gives the expected 1-allylcy-clopropene. These results are discussed with a view to the Lewis acidity of the gener-ated LiI and LiBr. — (KIM, R.; SHERRILL, W. M.; RUBIN*, M.; Tetrahedron 66 (2010) 27-28, 4947-4953, DOI:10.1016/j.tet.2010.04.123 ; Dep. Chem., Univ. Kans., Lawrence, KS 66045, USA; Eng.) — Klein
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ChemInform 2010, 41, issue 45 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cheminform.wiley-vch.de
ChemInform 2010, 41, issue 45 © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim