3375-38-0Relevant articles and documents
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Hill
, p. 4105 (1932)
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Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate
Sekiguchi, Yoshiya,Lee, Yan Ying,Yoshikai, Naohiko
supporting information, p. 5993 - 5997 (2021/08/16)
We report herein a nickel-catalyzed ring-opening allylation of cyclopropanols with allylic carbonates that occurs under mild and neutral conditions. The reaction displays linear selectivity for both linear and branched acyclic allylic carbonates and is also applicable to cyclic allylic carbonates, affording a variety of δ,?-unsaturated ketones in moderate to good yields. Mechanistic experiments are in accord with a catalytic cycle involving decarboxylative oxidative addition of allylic carbonate to Ni(0), alkoxide exchange with cyclopropanol, cyclopropoxide-to-homoenolate conversion on Ni(II), and C-C reductive elimination.
Rhodium-Catalyzed Room Temperature C-C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones
Ghosh, Asit,Pati, Bedadyuti Vedvyas,Ravikumar, P. C.
supporting information, (2020/04/02)
A rhodium-catalyzed room temperature C-C activation of cyclopropanol has been demonstrated for the single-step synthesis of a range of electronically and sterically distinct 1,6-diketones. This reaction proceeds efficiently in shorter reaction time following a highly atom-economical pathway. To illustrate the synthetic potential of 1,6-diketones, aldol and macrocyclization reactions have been successfully demonstrated. Preliminary mechanistic studies revealed the involvement of nonradical pathways.
AlCl3-mediated aldol cyclocondensation of 1,6- and 1,7-diones to cyclopentene and cyclohexene derivatives
Miyahara, Yuji,Ito, Yoshio N.
, p. 6801 - 6807 (2014/08/18)
Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,?-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)3, and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.