Destructive Alkylation of Phenol with Diisobutylene

Alkylation of phenol: a mechanistic view.

The current work utilizes the ab initio density functional theory (DFT) to develop a molecular level of the mechanistic understanding on the phenol alkylation in the presence of a cation-exchange resin catalyst, Amberlyst-15. The catalyst is modeled with the benzene sulfonic acid, and the effect of this acid on olefins such as isopropene (i-Pr) and tributene (t-Bu) in a phenol solution mimics t...

Friedel-Crafts alkylation of Phenol using Ionic Liquid as Catalyst

Highly selective metal mediated ortho-alkylation of phenol. First platinum containing organometallic chromane analogues.

We were able, for the first time, to synthesize and characterize Pt derivatives with a structural shape similar to vitamin E, having a metalla-chromane core. The formation reaction mechanism includes an unexpected highly selective ortho aromatic electrophilic substitution on phenol, operated by [PtCl(eta(1)-C(2)H(4)OR)(N-N)], R = Me or Ph, and a final cyclization step. The X-ray structure of on...

Diastereoselective phenol para-alkylation: access to a cross-conjugated cyclohexadienone en route to resiniferatoxin.

We document a route for the synthesis of a densely functionalized spiro-fused 2,5-cyclohexadienone as an intermediate for the synthesis of resineferatoxin. The strategy is based on an unprecedented diastereoselective, intramolecular phenol para-alkylation to a cross-conjugated cyclohexadienone. In the course of these synthetic studies we developed rapid access to a chiral nitrile possessing a q...

Zeolite catalyzed alkylation of toluene by alcohol

Vapor-phase methylation of toluene using methanol and its isopropylation with 2-propanol has been investigated ina down flow reactor under atmospheric conditions using N2 carrier over a series of surface modified andunmodified ZSM-5 (Si/Al= 60-170) loaded with H3PO4, differing in the external surface treatment of the zeolites.The feed molar ratios of toluene/methanol and toluene/2-propanol were...