The disproportionation reactions of various dialkyl diarylmethyl ethers have been carried out in the presence of a catalytic amount (10 mol-%) of o-benzenedisulfonimide as a Brønsted acid catalyst; the reaction conditions were mild, and the yields of the diarylmethane target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. The theoretical study confirmed that the reaction proceeds in two steps: The formation of a carbocation from the protonated ether followed by hydride transfer. Although the hydride transfer is the rate-determining step, it is the stability of the carbocation that determines the reaction rate and therefore the yields.

Synthetic and mechanistic aspects of acid-catalyzed diarylmethyl dialkyl ethers disproportionation. A combined experimental and theoretical study

BARBERO, Margherita;BAZZI, STEFANO;CADAMURO, Silvano;DUGHERA, Stefano;GHIGO, Giovanni
2009-01-01

Abstract

The disproportionation reactions of various dialkyl diarylmethyl ethers have been carried out in the presence of a catalytic amount (10 mol-%) of o-benzenedisulfonimide as a Brønsted acid catalyst; the reaction conditions were mild, and the yields of the diarylmethane target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. The theoretical study confirmed that the reaction proceeds in two steps: The formation of a carbocation from the protonated ether followed by hydride transfer. Although the hydride transfer is the rate-determining step, it is the stability of the carbocation that determines the reaction rate and therefore the yields.
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4346
4351
http://www.eurjoc.org
Homogeneous catalysis; Ethers; Density functional calculations; Disproportionation; Reaction mechanisms
Margherita Barbero; Stefano Bazzi; Silvano Cadamuro; Stefano Dughera; Giovanni Ghigo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/60848
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