Heterocyclic Vinyl Ethers. III. The Synthesis of 1,4-Dithiadiene and 1,4-Dithiadiene Disulfone^1-3

A New Dithiophene Fused p-Phenylene Vinylene Conducting Polymer. Synthesis and Study

“…The mixture was cooled to -78 'C and 12.5 mL of 1.6 M of n-BuLi in hexanes (0.02 mol) was added dropwise in about 15 min. The mixture was stirred for 30 min, 2,2,2'2'-tetramethoxyethyldisulfide (3) (4.84g, 0.02 mol), prepared essentially as reported, 8 in 5 mL of dry THF was added dropwise over about 15 min and the mixture was stirred for 30 additional min. The second part of the n-BuLi (13.75 mL, 1.6 M, 0.022 mol) was added dropwise in about 15 min, and the mixture was stirred for 30 min.…”

“…Synthesis of poly(p-phenylene vinylene) polymers through the soluble precursor polymer containing a sulfonium salt in the repeat unit has become standard methodology for the preparation of such polymers. 9 -1 3 Our synthesis involves reacting 2,2,2'2'-tetramethoxyethyldisulfide(3), prepared essentially as reported,8 with the lithium derivative of 2,5-dibromo-p-xylene and then repeating this reaction to give 2,5-bis(2,2-dimethoxyethylthio)-1,4-dimethylbenzene (4) which was cyclized to 4,8-dimethylbenzol 1,2-b:4,5-bldithiophene (5) using polyphosphoric acid. It should be mentioned that two unsaturated side products were formed in the preparation of 4, which are the enol ethers formed by elimination of one and two molecules of methanol from 4.…”

Rearrangement of chlorinated β‐diketone monomethyl enol ethers with sodium methoxide

“…However at reflux temperature the reaction product was 3-hydroxy-2,4,4-trimethoxy-l-pentene (5) along with a minor amount (maximum 5 % ) of Favorskii-rearrangement products 5, 1, (8, E and 2 isomers, possible artifacts from decomposition of 6 ) . When the reaction was carried out at room temperature for 24 hours a higher amount (15 % ) of these esters was obtained.…”

Quantum chemical estimation of the macrocyclization of 1,4-dithiine

“…Lewi called his compound biophene and described its physical and chemical properties. However, he seems to deal with a completely different compound because later works described completely different physicochemical and spectral properties of this compound [2,3]. At present, interest in 1,4-dithiine and similar compounds is due to a potential opportunity to use these molecules for the preparation of nanosized macrocycles that can be applied in both microelectronics and pharmacology.…”