Journal
TETRAHEDRON
Volume 64, Issue 22, Pages 5156-5161Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.03.049
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A highly stereoselective synthesis of exo-spiro[cyclopropane-1,4'-pyrazolin-5'-one] from 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one and arsonium bromide in the presence of base has been achieved. The triphenylarsine-catalyzed cyclopropanation of 4-arylidene-3-methyl-1-phenyl-pyrazolin-5-one with bromide in the presence of NaHCO3 has also been studied. Both exo and endo isomers were formed in this reaction. The structures of the products were characterized by IR, MS, H-1 NMR, elemental analysis, and X-ray diffraction analysis.
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