29275-82-9Relevant academic research and scientific papers
Boosting effect of ortho-propenyl substituent on the antioxidant activity of natural phenols
Marteau, Clémentine,Guitard, Romain,Penverne, Christophe,Favier, Dominique,Nardello-Rataj, Véronique,Aubry, Jean-Marie
, p. 418 - 427 (2016)
Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects.
A concise synthesis of carpanone using solid-supported reagents and scavengers
Baxendale, Ian R.,Lee, Ai-Lan,Ley, Steven V.
, p. 1850 - 1857 (2007/10/03)
The synthesis of the natural product carpanone by utilization of polymer supported reagents, eliminating the need for conventional purification techniques was reported. The synthesis and crystal structure of a polymer-supported iridium catalyst for isomerization was also reported. The observations showed that isomerization of electron-rich aromatic compounds by the catalyst resulted in products with predominantly trans alkene geometry. However, the electron-poor derivatives were found to be less prone to rearrangement.
