56759-60-5Relevant articles and documents
Nuclear versus side-chain bromination of 4-methoxy toluene by an electrochemical method
Kulangiappar,Anbukulandainathan,Raju
, p. 2494 - 2502 (2014/08/05)
GRAPHICAL ABSTRACT The electrochemical bromination of 4-methoxy toluene by two-phase electrolysis yields 3-bromo 4-methoxy toluene at first, which subsequently undergoes side-chain bromination to give 3-bromo 4-methoxy benzyl bromide as a final product in 86% yield. The two-phase electrolysis consists of 25-50% NaBr as aqueous electrolyte and CHCl3 containing aromatic compound as organic phase. The reaction temperature is maintained at 10-25 °C. The probable orientation of bromine atom in an alkyl aromatic compound (nuclear versus side chain) is explained from the experimental result.
Vanadium-catalyzed oxidative aromatization of 2-cyclohexenones under molecular oxygen
Moriuchi, Toshiyuki,Kikushima, Kotaro,Kajikawa, Tomomi,Hirao, Toshikazu
supporting information; experimental part, p. 7385 - 7387 (2010/01/18)
An efficient catalytic oxidative aromatization of 2-cyclohexenones was achieved by a combination of a commercially available inexpensive ligand-free vanadium catalyst, a bromide source, and an acid under atmospheric oxygen to afford the corresponding phenol derivatives. This catalytic oxidative aromatization proceeded even under air. Furthermore, a gram-scale reaction was performed successfully.
Understanding solid/solid organic reactions
Rothenberg,Downie,Raston,Scott
, p. 8701 - 8708 (2007/10/03)
The concept of an organic reaction between two macroscopic solid particles is investigated. Thus, we study several reactions that have been recently reported to proceed "in the solid phase" and clearly show that, in most cases, grinding the two solid reactants together results in the formation of a liquid phase. This is true both for catalytic transformations (e.g., aldol condensations and oligomerization of benzylic compounds) and for noncatalytic reactions (Baeyer - Villiger oxidations, oxidative coupling of naphthols using iron chloride, condensation of amines and aldehydes to form azomethines, homo-etherification of benzylic alcohols using p-toluenesulfonic acid, and nuclear aromatic bromination with NBS). This liquefaction implies the existence of a eutectic mixture with Tfusion below ambient temperature (although both reagents have higher than ambient melting points). In cases where heating is required, it is again clear that a phase change (from solid to liquid) occurs, explaining the observed reaction kinetics. On the basis of 19 experimental examples, we discuss the possibility of solid-phase organic reactions and the implications of these findings to the reaction between two solid reagents. A general description of such reactive systems is proposed, based on a consideration of the potential for eutectic (or peritectic) formation between the constituents of the liquid phases that arise during the process of mechanical mixing of the solid reagents and products.