Three-membered ring formation—IV
1973; Elsevier BV; Volume: 29; Issue: 9 Linguagem: Inglês
10.1016/0040-4020(73)80098-5
ISSN1464-5416
AutoresYusuke Kawakami, Keisuke Tajima, Teiji Tsuruta,
Tópico(s)Cyclopropane Reaction Mechanisms
ResumoSelective syntheses for some 1-halogeno-2-alkyl-cis-1,2-cyclopropanedicarboxylic esters were studied. In a ring formation between α-halogenoacetic and α-propylacrylic esters, lithium hydride was a much better condensing agent than sodium hydride for the selective syntheses of cyclopropanedicarboxylic ester possessing two different alcohol residues. A greater reactivity was found at the ester group linked to carbon 1 than that linked to carbon 2 in transesterification by alkali metal t-butoxide and also in its partial hydrolysis by KOH. This is presumably ascribed to the difference in the inductive effects of alkyl group and the Cl atom.
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