27608-11-3Relevant articles and documents
Indium/copper-mediated conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds in water
Shen, Zhi-Liang,Cheong, Hao-Lun,Loh, Teck-Peng
supporting information; scheme or table, p. 1051 - 1054 (2009/05/27)
An efficient method for the conjugate addition of unactivated alkyl iodides to α,β-unsaturated carbonyl compounds using indium/copper in water is described. The reactions proceed more efficiently in water than in organic solvents. In, CuI, and InCl3
Regioselective radical ring-opening reaction of bicyclo[4.2.0]octan-2-ones promoted by samarium(II) iodide
Kakiuchi, Kiyomi,Minato, Koichi,Tsutsumi, Ken,Morimoto, Tsumoru,Kurosawa, Hideo
, p. 1963 - 1966 (2007/10/03)
Radical ring-opening reactions of bicyclo[4.2.0]octanones, its C6 alkyl derivatives, and tricyclic ketones promoted by SmI2 gave cyclohexanones via fission of the external cyclobutane bond. The CO2Me, CN, and phenyl derivatives led t
Reductive free-radical alkylations and cyclisations mediated by 1-alkylcyclohexa-2,5-diene-1-carboxylic acids
Baguley, Paul A.,Walton, John C.
, p. 2073 - 2082 (2007/10/03)
A range of 1-alkylcyclohexa-2,5-diene-1-carboxylic acids were prepared by Birch reduction-alkylation of benzoic acid and their efficiency as mediators of alkyl radical chain addition and cyclisation processes was investigated. Reductive alkylations were respectably successful, even with only one or two equivalents of alkene, for secondary, tertiary and benzylic radicals. Reaction of 1-[2-(cyclohex-2-enyloxy)ethyl]cyclohexa-2,5-diene-1-carboxylic acid yielded the product of exo-trig-cyclisation, i.e. 7-oxabicyclo[4.3.0]nonane, in a yield comparable to that obtained from the tributyltin hydride induced cyclisation of 3-(2′-iodoethoxy)-cyclohexene. This, together with the isolation of both exo- and endo-cyclisation products from 1-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethoxy)ethyl]cyclohexa-2,5-diene- 1-carboxylic acid established that ring closures could also be satisfactorily mediated with these reagents. Preparations were completely free of metal contaminants and direct reduction of the alkyl radicals, prior to addition or cyclisation, was completely absent. However, the desired products were accompanied by alkylbenzenes, together with by-products from the initiator decompositions, and this complicated work-up. Failure to obtain 1-[2-(prop-2-yn-1-yloxy)cyclohexyl]cyclohexa-2,5-diene-1-carboxylic acid in Birch reductive alkylations with trans-1-iodo-2-(prop-2-yn-1-yloxy)cyclohexane (and the corresponding bromide) indicated a limitation on precursor synthesis. The Birch reduction-alkylation was not of universal applicability and was suppressed for alkyl halides having β-substituents.
