Synthesis and conformational aspects of 2-phenoxytetralones: Experimental verification and density functional theory (DFT) calculation

A series of 2-phenoxy-1-tetralones have been synthesized as conformationally constrained analogs of bioactive compounds 2-phenoxyacetophenones. A representative oxime derivative of 2-(3-methoxyphenoxy)-1-tetralone was selectively prepared and its ( Z ) -geometry was characterized by proton nuclear magnetic resonance ( 1 H NMR) spectroscopy. Also, the conformational aspects of designed compounds were investigated by 1 H NMR spectroscopy and density functional theory (DFT) calculations. The computational results showed that the more stable conformation in 5c is a conformer with equatorial orientation for 2-aryloxy group but the axial orientation in the related oxime 6 is predominated. Accordingly, it was demonstrated that the formation of ( Z )-oxime on 1position results in a remarkable conformational inversion on tetralin ring.