- HOTf mediated cascade reactions of 1-arenoylcyclopropanecarboxylic acids with arenes
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The cascade reactions of 1-arenoylcyclopropanecarboxylic acids with arenes proceed smoothly in freshly distilled HOTf to give the corresponding tetrahydro-5H-benzo[c]fluorene derivatives in good yields along with high stereoselectivities under mild conditions. The Royal Society of Chemistry.
- Chen, Gen-Qiang,Tang, Xiang-Ying,Shi, Min
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p. 2340 - 2342
(2012/04/18)
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- Dimerization of Cyclopropanecarboxylic Acid Dianion and Thermal Decarboxylative Rearrangement of the Dimer to 2-Cyclopropyl-4,5-dihydrofuran
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The dianion of cyclopropanecarboxylic acid (2) reacted with alkyl halides and deuterated water at temperatures below 0 deg C; however, self-condensation to the β-keto acid 3 was the only observed product at elevated temperatures.This observation contrasts the self-condensation of the ethyl ester where a trimeric diester alcohol is the product.Attempted mixed condensations of the dianion 2 and carboxylic acids without acidic α-protons did not proceed as well, 3 being the major product.Thermal decarboxylation of 3 did not yield the expected dicyclopropyl ketone; rather , a facile rearrangement in a sealed tube at 120 deg C occured, giving rise to 2-cyclopropyl-4,5-dihydrofuran.This "vinyl-cyclopropyl" type rearrangement does not occur through dicyclopropyl ketone or its enolate.
- Jahngen, Edwin G. E.,Phillips, Douglas,Kobelski, Robert J.,Demko, Donald M.
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p. 2472 - 2476
(2007/10/02)
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