Molecules 2012, 17(3), 2579-2586; doi:10.3390/molecules17032579
Communication

Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold

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Received: 13 February 2012; in revised form: 21 February 2012 / Accepted: 22 February 2012 / Published: 2 March 2012
(This article belongs to the Special Issue Gold Catalysts)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: (1R*,4S*,4aR*,9aS*,10S*)-10-Hydroxy-10-phenyl-1,4a,9a,10-tetrahydro-1,4-methanoanthracen-9(4H)-one (1c) was prepared for the elucidation of the reaction mechanism of intramolecular hydroalkoxylation of alkenes catalyzed by gold nanoclusters stabilized by a hydrophilic polymer, poly(N-vinyl-2-pyrrolidone) (Au:PVP). It was found that the reaction proceeded via anti-addition of alcohol to the alkene assisted by p-activation of the gold clusters, which is the same mechanism as the hydroamination by toluenesulfonamides.
Keywords: gold nanoclusters; hydroalkoxylation; anti-addition; p-activation
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MDPI and ACS Style

Kitahara, H.; Sakurai, H. Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold. Molecules 2012, 17, 2579-2586.

AMA Style

Kitahara H, Sakurai H. Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold. Molecules. 2012; 17(3):2579-2586.

Chicago/Turabian Style

Kitahara, Hiroaki; Sakurai, Hidehiro. 2012. "Anti-Addition Mechanism in the Intramolecular Hydroalkoxylation of Alkenes Catalyzed by PVP-Stabilized Nanogold." Molecules 17, no. 3: 2579-2586.

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