68593-72-6Relevant academic research and scientific papers
A 'meta effect' in the fragmentation reactions of ionised alkyl phenols and alkyl anisoles
Bouchoux, Guy,Sablier, Michel,Miyakoshi, Tetsuo,Honda, Takashi
, p. 539 - 546 (2012/09/22)
The competition between benzylic cleavage (simple bond fission [SBF]) and retro-ene rearrangement (RER) from ionised ortho, meta and para RC 6H4OH and RC6H4OCH3 (R = n-C3H7, n-C4H9, n-C5H11, n-C7H15, n-C9H19, n-C 15H31) is examined. It is observed that the SBF/RER ratio is significantly influenced by the position of the substituent on the aromatic ring. As a rule, phenols and anisoles substituted by an alkyl group in meta position lead to more abundant methylene-2,4-cyclohexadiene cations (RER fragmentation) than their ortho and para homologues. This 'meta effect' is explained on the basis of energetic and kinetic of the two reaction channels. Quantum chemistry computations have been used to provide estimate of the thermochemistry associated with these two fragmentation routes. G3B3 calculation shows that a hydroxy or a methoxy group in the meta position destabilises the SBF and stabilises the RER product ions. Modelling of the SBF/RER intensities ratio has been performed assuming two single reaction rates for both fragmentation processes and computing them within the statistical RRKM formalism in the case of ortho, meta and para butyl phenols. It is clearly demonstrated that, combining thermochemistry and kinetics, the inequality (SBF/RER) metaorthopara holds for the butyl phenols series. It is expected that the 'meta effect' described in this study enables unequivocal identification of meta isomers from ortho and para isomers not only of alkyl phenols and alkyl anisoles but also in other alkyl benzene series. Copyright
Overbased sulfurized alkaline earth metal phenates and process for preparing same
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, (2008/06/13)
Overbased sulfurized alkaline earth metal phenates which are oil soluble, excellent in detergency dispersancy and have high base value, and an effective process for production of said overbased sulfurized alkaline earth metal phenates under conditions providing less sludge and less raw material recovery, and further a lubricating oil additives containing said overbased sulfurized alkaline earth metal phenates as a main ingredient and a lubricating oil composition which comprises said lubricating oil additive compounded in a lubricating oil are disclosed. Since the resulting overbased sulfurized alkaline earth metal phenates have high base value and excellent oil-solubility, they can be effectively utilized as lubricating oil additives.
Analogues of Poison Ivy Urushiol. Synthesis and Biological Activity of Disubstituted n-Alkylbenzenes
ElSohly, Mahmoud A.,Adawadkar, Prakash D.,Benigni, Daniel A.,Watson, Edna S.,Little, Thomas L.
, p. 606 - 611 (2007/10/02)
The total synthesis of different isomers and analogues of poison ivy urushiol is described.These include the positional isomers 1-5 and the nitrogen-containing analogues 6 and 8 and their mesylamino derivatives 7 and 9. 3,4-Dimethoxybenzaldehyde, m-dimeth
