Variations of solvent and substitution pattern in Pb (OAc) 4 mediated domino reactions

…, JIC Lena, E Altınel, N Birlirakis, S Arseniyadis

Index: Sesenoglu, Oezge; Candela Lena, Jose I.; Altinel, Ertan; Birlirakis, Nicolas; Arseniyadis, Simeon Tetrahedron Asymmetry, 2005 , vol. 16, # 5 p. 995 - 1015

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Citation Number: 12

Abstract

The effect of solvent on oxidative cleavage of the Hajos–Parrish ketone derived hydrindene– diols 1, and Wieland–Miescher ketone derived octaline–diols 2 with Pb (OAc) 4 is presented. Various solvents were screened and compared for these domino reactions. Changing the solvent influenced the reaction rate, product distribution, and chemical yield in the octalin–diol series, while no-effect was detected in the lower homologue hydrindene– ...