Stereostructure and thermodynamic stability of atropisomers of ortho-substituted 2, 2′-diaryl-1, 1′-binaphthalenes

M Ehn, NG Vassilev, P Kasak, B Horvath, J Filo…

Index: Ehn, Marcel; Vassilev, Nikolay Georgiev; Kasak, Peter; Horvath, Branislav; Filo, Juraj; Mereiter, Kurt; Rakovsky, Erik; Putala, Martin Tetrahedron Asymmetry, 2013 , vol. 24, # 20 p. 1303 - 1311

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Abstract

Abstract A series of ortho-substituted 2, 2′-aryl-1, 1′-binaphthalenes were prepared via Negishi arylation of 2, 2′-diiodo-1, 1′-binaphthalene in good to high yields (65–95%) as an equilibrium mixtures of up to three atropisomers (unlike, unlike, like, unlike, and like, like). Thermodynamic stability parameters of the atropisomers were evaluated from VT NMR spectra by regression analysis. The DFT parameters calculated using CAM-B3LYP ...