83385-86-8

Upstream product

• 108-68-9 3,5-Dimethylphenol 

Downstream Products

• 83385-82-4 2,6-dibromo-3,5-dimethylanisole 
• 1384524-22-4 C₁₁H₁₃Br₂NOS 

Relevant academic research and scientific papers

Benzyne 1,2,4-Trisubstitution and Dearomative 1,2,4-Trifunctionalization

Both 1,2,4-trisubstitution and dearomative 1,2,4-trifunctionalization of benzyne have been accomplished from sulfoxides bearing a penta-2,4-dien-1-yl moiety. These cascade transformations proceed through a benzyne insertion into the S═O bond and an uncommon regiospecific anionic [4,5]-sigmatropic rearrangement, furnishing a C-O, C-S, and C-C bond on the C1-, C2-, and C4-position of a benzene ring, respectively. This study showcases new cascade benzyne reaction modes involving both distal C-H bond functionalization and dearomatization.

Synthesis of a new chiral sulfonic acid

A convenient route to an original chiral sulfonic acid is disclosed. The synthesis is based on an optimized and regioselective direct bis-orthoarylation of a commercially available phenol, followed by a Newman-Kwart rearrangement. Resolution by preparative chiral HPLC and oxidative cleavage give the targeted Brnsted acid in >99% ee. Georg Thieme Verlag Stuttgart · New York.

Understanding solid/solid organic reactions

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.

Restricted Rotation Involving the Tetrahedron Carbon. XLIII. Buttressing Effect on Rotational Barriers in Bromine-substituted 9-(2-Methoxy-4,6-dimethylphenyl)fluorenes

9-(2-Methoxy-4,6-dimethylphenyl)fluorenes carrying one or two bromo groups on the phenyl ring were prepared and the buttressing effect on the rotational barrier about the C9-Cph bond were investigated.The free energies of activation