Superacid-catalyzed reactions of cinnamic acids and the role of superelectrophiles.

  title={Superacid-catalyzed reactions of cinnamic acids and the role of superelectrophiles.},
  author={Rendy Rendy and Yun Zhang and Aaron McElrea and Alma Gomez and Douglas A. Klumpp},
  journal={The Journal of organic chemistry},
  volume={69 7},
The chemistry of cinnamic acids and related compounds has been studied. In superacid-catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature (13)C NMR) is reported. We provide clear evidence that protonated carboxylic acid groups (or the… 

Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles.

Olefinic pyrazines are found to react with benzene in CF3SO3H and give anti-Markovnikov-type addition products and it is suggested that acid-catalyzed addition reactions can giveAnti-MarkOVnikov- type products when a multiply charged group is adjacent to the olefinics site.

Reactions of acetylene ketones in superacids

Vinyl type cations ArC+=CHCOR generated from acetylene ketones ArC≡CCOR in superacids HSO3F and CF3SO3H react with diverse benzene derivatives to form alkenylation products, E-/Z-isomers of

Rh-Catalyzed Annulation of Benzoic Acids, Formaldehyde, and Malonates via ortho-Hydroarylation to Indanones.

A three-component reaction from readily available low-cost materials of benzoic acids, formaldehyde, and malonates for the preparation of indanones by rhodium catalysis is reported. The annulation is

Reactions of arylacetylenic compounds with arenes in the presence of aluminum halides

Conjugated arylacetylenic ketones and aldehydes, propargyl-type alcohols, and arylacetylenes reacted with arenes in the presence of AlBr3 or AlCl3 as catalyst to give substituted indenes.

Superacid mediated intramolecular condensation: facile synthesis of indenones and indanones

Superacid promoted intramolecular acylation is described for the synthesis of indenones. Interestingly, in all resulting indenones, the olefin bond is rearranged to the exo position of the five

Electrophilic activation of acetylene compounds in Brønsted superacids. Reactions of vinyl type cations

Published data on the reactions of vinyl type cations generated upon protonation of the carbon–carbon triple bond of acetylene compounds in proton-donor Brønsted superacids and conjugate


Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles1

  • 2004