Ru complexes containing N-methyl-1,3,5-triaza-7-phosphaadamantane (mPTA) as catalysts for the isomerization of 2-cyclohexen-1-ol.
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Lopez-Sánchez, Belen; Bohome-Espinosa, Ana Belén; Scalambra, Franco; Romerosa Nievas, Antonio ManuelDate
2022Abstract
The complex [RuCp(H2O-κO)(mPTA)2](CF3SO3)3 MeOH (4 MeOH) was synthesized
and characterized by spectroscopic techniques and its crystal structure
determined by single-crystal X-ray diffraction (mPTA = N-methyl-1,3,5-triaza-
7-phosphaadamantane). The catalytic activity of 4 for the redox isomerization
of 2-cyclohexen-1-ol into cyclohexanone was studied in water, methanol/
water, and biphasic systems, reaching the highest conversion rate in biphasic
water/cyclohexane (1:1) at pH 1.7 and under N2. The aqueous phase containing
4 was recycled up to 7 consecutive runs, reaching a total turnover number
(TON) of 471 without significant losses of catalyst. Therefore, this reaction is a
unique procedure for the isomerization of cyclic allylic alcohols without metal
contamination of the product. The catalytic reaction mechanism was studied
by nuclear magnetic resonance (NMR), showing that the reaction probably
proceeds through the formation of an intermediate in which the substrate is
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Palabra/s clave
Ru complexes
catalysts
isomerization of 2-cyclohexen-1-ol