193153-69-4

Upstream product

• 636-09-9 diethyl terephthalate 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 193153-80-9 3-(2,6-dimethoxybenzoyl)-3-(2,6-dimethoxyphenyl)-6-[bis(2,6-dimethoxyphenyl)methylene]-1,4-cyclohexadiene 
• 193153-82-1 3-(2,6-dimethoxybenzoyl)-6-[bis(2,6-dimethoxyphenyl)methylene]-3-(4-methoxyphenyl)-1,4-cyclohexadiene 
• 193153-73-0 α,α,α',α'-tetrakis(2,6-dimethoxyphenyl)-1,4-benzenedimethanol 
• 193153-76-3 α,α,α'-tris(2,6-dimethoxyphenyl)-α'-(4-methoxyphenyl)-1,4-benzenedimethanol 
• 193153-75-2 α,α,α'-tris(2,6-dimethoxyphenyl)-α'-p-tolyl-1,4-benzenedimethanol 

Relevant academic research and scientific papers

Formation of 3-Methylene-1,4-cyclohexadienes from α,α,α',α'-Tetraaryl-1,4-benzenedimethanols by the Intramolecular Migration of an Aryl Group

By reactions of diethyl p-phthalate with 2,6-dimethoxyphenyllithium, ΦLi, a tri-substituted compound, p-HOCΦ2C6H4C(O)Φ (1), or tetra-substituted 1,4-benzenedimethanol, p-HOCΦ2C6H4CΦ2OH (2a), were obtained. Compound 1 further reacted with aryllithium, ArLi, to give the 1,4-benzenedimethanols, p-HOCΦ2C6H4CArΦOH (Ar = 4-MeC6H4 2b, 4-MeOC6H4 2c). When 2a was treated with acid in dimethyl sulfoxide, 3-(2,6-dimethoxybenzoyl)-3-(2,6-dimethoxyphenyl)-6-[bis(2,6-dimethoxyphenyl) methylene]-1,4-cyclohexadiene, Φ2C chemical equation presented (4a) was obtained in quantitative yield under a variety of conditions. The reaction is understood to involve an initial formation of carbenium ion, [p-Φ2C+-C6H4CΦ 2OH] (3a), of which the positive charge must be partly shared with the other end of the p-phenylene ring, where one of the neighboring Φ-groups migrates. Reactions in acetone resulted to give 4a or dark-violet crystals of (2′,6′-dimethoxy-4-biphenylyl)bis(2,6-dimethoxyphenyl)carbenium perchlorate, [(4-ΦC6H4)CΦ2]ClO4, depending on the reaction conditions. Reactions in methanol, ethanol, or in hot 2-propanol resulted to give the reduced compound, (4-ΦC6H4)Φ2CH. The 1,4-benzenedimethanols, 2b and 2c, also reacted with perchloric acid in dimethyl sulfoxide to form the 3-methylene-1,4-cyclohexadiene derivatives, Φ2C chemical equation presented (Ar = 4-MeC6H4 4b, 4-MeOC6H4 4c), respectively. Evidence is given by the 1H NMR spectrum, which shows the formation of intermediate carbenium ions 3a - c.