Dinuclear barium(II) complexes based on a calix[4]arene scaffold as catalysts of acyl transfer

Chemistry : a European Journal
Roberta CacciapagliaRocco Ungaro

Abstract

Two novel regioisomeric calix[4]arene derivatives (2 and 3), decorated with two aza[18]crown-6 units at vicinal (1,2) or diagonal (1,3) positions of the upper rim, were synthesized. The catalytic activities of their dinuclear Ba2+ complexes were investigated in the ethanolysis of esters 8-11, endowed with a carboxylate anchoring group. Major results are as follows: 1) the two metal ions in the dinuclear catalysts work together in a cooperative fashion; 2) the vicinal calix[4]arene catalyst 2 is far superior to its diagonal regioisomer 3 in the reactions of all of the investigated esters; and 3) the distance between the carboxylate and ester carbonyl, which increases regularly from 8 to 11, influences reactivity of catalytic ester cleavage in a way that is decidedly suggestive of the importance of a good match between ester size and metal-to-metal distance. However, the superiority of the vicinal catalyst 2 relative to 3 cannot be explained on the basis of the putative match of ester size to intermetal distance, thus providing an indication that additional, still poorly understood effects may contribute significantly to catalytic efficiency.

References

Aug 21, 2001·The Journal of Organic Chemistry·R CacciapagliaL Mandolini
Feb 20, 2003·Journal of the American Chemical Society·Roberta CacciapagliaLuigi Mandolini
Feb 18, 2004·Accounts of Chemical Research·Roberta CacciapagliaLuigi Mandolini
Feb 1, 1999·Angewandte Chemie·Roberta CacciapagliaLuigi Mandolini

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Citations

Oct 20, 2015·Organic & Biomolecular Chemistry·Varun RawatArkadi Vigalok
Sep 14, 2012·Chemical Society Reviews·Zeyuan DongJunqiu Liu
Dec 25, 2013·Chemical Society Reviews·Matthieu RaynalPiet W N M van Leeuwen
Oct 30, 2008·Chemical Reviews·Damien M Homden, Carl Redshaw
Mar 1, 2012·The Journal of Organic Chemistry·Laura BaldiniRocco Ungaro
Jan 18, 2005·The Journal of Organic Chemistry·Roberta CacciapagliaRocco Ungaro

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