ChemInform Abstract: Multi‐Channel Transformations of 1,3‐Diarylpropynones under Superelectrophilic Activation Conditions: Concurrence of Intra‐ and Intermolecular Reactions. Experimental and Theoretical Study.

Dmitry S Ryabukhin,Aleksander V Vasilyev,Georgy K Fukin

doi:10.1002/chin.201512132

ChemInform Abstract: Multi‐Channel Transformations of 1,3‐Diarylpropynones under Superelectrophilic Activation Conditions: Concurrence of Intra‐ and Intermolecular Reactions. Experimental and Theoretical Study.

Dmitry S Ryabukhin, Aleksander V Vasilyev + Show 1 more

https://doi.org/10.1002/chin.201512132

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Journal: ChemInform

Publication Date: Mar 1, 2015

Affiliation: St Petersburg University

#HF SbF5 #Orbital Contributions + Show 8 more

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Abstract

Abstract 1,3-Diarypropynones undergo concurrent multi-channel transformations in Bronsted (FSO3H, TfOH) and Bronsted–Lewis (HF–SbF5, TfOH-SbF5) superacids, leading intramolecularly to 3-arylindenones, or intermolecularly to 1,3,3-triarylpropenones, and dimeric structures. The outcome depends on the electronic donor-acceptor properties of the substituents in the aromatic rings of the 1,3-diarylpropynones, and on the added aromatic external π-nucleophiles. The orbital energies, atom charges, orbital contributions, and global electrophilicity indices of the cationic intermediates have been calculated by DFT methods to explain these transformations.

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