96997-55-6Relevant academic research and scientific papers
Regioselective dehydration in cyclic system with triphenylphosphine-azodicarboxylate
Iimori,Ohtsuka,Oishi
, p. 1209 - 1212 (1991)
The regioselective dehydration of cyclohexanol derivatives was achieved by using the Mitsunobu reagent system. The reaction undergoes under mild and neutral conditions. The observed regioselectivity was explained by considering the importance of the orientation of the leaving group at the elimination stage.
Stereoelectronic Effects in Hydrogen-atom Transfer Reactions of Substituted Cyclohexyl Radicals
Beckwith, Athelstan L. J.,Easton, Christopher J.
, p. 661 - 668 (2007/10/02)
Thermolysis of the peroxyoxalates (1)-(7) and the diacyl peroxides (8)-(11) in cyclohexane at 100 deg C gives cycloalkenes and cycloalkanes by hydrogen-atom transfer reactions of the initially formed conformationally biased 4-t-butyl-, 4-t-butyl-cis,cis-2,6-dimethyl-, 4-t-butyl-cis,trans-2,6-dimethyl-, 4-t-butyl-cis-2-methyl-, 4-t-butyl-trans-2-methyl-, and 5-t-butyl-cis-2-methylcyclohexyl radicals (12)-(17).The composition of the product mixtures indicates that transfer of axial β-hydrogen atoms occurs more rapidly than does transfer of equatorial β-hydrogen atoms.These results support the hypothesis that homolytic fission of a C-H bond is favoured when it lies chlose to the plane of an adjacent semi-occupied orbital.
