Journal
TETRAHEDRON
Volume 70, Issue 43, Pages 7865-7873Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.09.006
Keywords
Superelectrophilic activation; Bronsted superacids; 1,3-Diarylpropynones; 3-Arylindenones; 1,3,3-Triarylprop-2-en-1-ones; DFT calculations
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Funding
- Russian Foundation for Basic Research [12-03-00311-a]
- Saint Petersburg State University [12.50.1558.2013, 12.38.195.2014]
- Russian Scientific Fund [14-13-00832]
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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 pi-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. (C) 2014 Elsevier Ltd. All rights reserved.
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