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Issue 24, 2018
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The role of proton shuttling mechanisms in solvent-free and catalyst-free acetalization reactions of imines

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Abstract

Proton transfer is central to the understanding of chemical processes. More so in addition reactions of the type NuH + E → Nu–EH taking place under solvent-free and catalyst-free conditions. Herein we show that the addition of alcohols or amines (the NuH component) to imine derivatives (the E component), in 1 : 1 ratio, under solvent-free and catalyst-free conditions, are efficient methods to access N,O and N,N-acetal derivatives. In addition, computational studies reveal that they are catalyzed reactions involving two or even three NuH molecules operating in a cooperative manner as H-bonded NuH⋯(NuH)n⋯NuH associates (many body effects) in the transition state through a concerted proton shuttling mechanism (addition of alcohols) or stepwise proton shuttling mechanism (addition of amines), thereby facilitating the key proton transfer step.

Graphical abstract: The role of proton shuttling mechanisms in solvent-free and catalyst-free acetalization reactions of imines

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Publication details

The article was received on 30 Apr 2018, accepted on 29 May 2018 and first published on 30 May 2018


Article type: Paper
DOI: 10.1039/C8OB01007B
Citation: Org. Biomol. Chem., 2018,16, 4527-4536
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    The role of proton shuttling mechanisms in solvent-free and catalyst-free acetalization reactions of imines

    V. J. Lillo, J. Mansilla and J. M. Saá, Org. Biomol. Chem., 2018, 16, 4527
    DOI: 10.1039/C8OB01007B

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