86692-89-9Relevant academic research and scientific papers
Oxidativ Coupling of Phenols. Part 6. A Study of the Role of Spin Density Factors on the Product Composition in the Oxidations of 3,5-Dimethylphenol and Phenol
Armstrong, David R.,Cameron, Colin,Nonhebel, Derek C.,Perkins, Peter G.
, p. 563 - 568 (2007/10/02)
Oxidations of both 3,5-dimethyphenol and phenol with di-t-butyl peroxide at 140 degC gave as the major product the ortho-ortho-C-C coupled dimer, while oxidations with di-t-butyl peroxyoxalate at room temperature give much more of the ortho-para-C-C dimer.The results are not consistent either with the spin density distribution in the phenoxyl radical intermediates or with steric effects being the major factor which determines the product composition.It is proposed that the two phenoxyl radicals involved in coupling preferentially approach each other in a 'sandwich like' manner with the oxigens in a 1,3-relationship.
THE ROLE OF STEREOELECTRONIC FACTORS IN THE OXIDATION OF PHENOLS
Armstrong, David R.,Breckenridge, Robin J.,Cameron, Colin,Nonhebel, Derek C.,Pauson, Peter L.,Perkins, Peter G.
, p. 1071 - 1074 (2007/10/02)
The oxidative coupling of both 3,5-dimethylphenol and phenol leads to the ortho-ortho and ortho-para coupled products as the predominant C-C dimers: stereoelectronic factors determine the preferred mode of approach of the phenoxyl radicals.
