Weygand, Friedrich published the artcileDehalogenation with sodium mercaptides, Category: bromides-buliding-blocks, the publication is Rev. Chim., Acad. Rep. Populaire Roumaine (1962), 7(2), 1379-92, database is CAplus.
The reactions of vicinal dihalides with mercaptides, leading to olefins or bis(alkyl- or arylthio) compounds were investigated and interpreted. The results indicated that the olefin-forming dehalogenation of vicinal dihalides was especially easy in compounds substituted with electron-attracting groups. The NaSEt suspension used was prepared by conversion of Na in ether with 10% excess EtSH. Dropwise addition of Me dibromodihydrocinnamate in ether to the mercaptide suspension gave Me cinnamate in 100% yield, also obtained in 82% yield with NaSPh. Dibenzalacetone was obtained in a similar manner in 80% yield from dibenzalacetone tetrabromide, coumarin in 97%, yield from 3,4-dibromodihydrocoumarin, and cholesterol in 93% yield from 5,6-dibromocholesterol and NaSEt. Reactions of the thiophenolate with 2,3-dimethyl-2,3-dibromobutane gave tetramethylethylene in 100% yield, with 2,3-dibromobutane, 2-butene in 72% yield, with 1,2-diiodoethane (heating), ethylene in 76% yield and with hexachloroethane (heating), tetrachloroethylene in 69% yield. In order to examine the stereospecificity of the dehalogenation, the di-Me dl- and meso-dibromosuccinate were converted with NaSEt in ether, to give di Me maleate and fumarate, resp., indicating that trans elimination occurred. No elimination by olefin formation but substitution was the result when 1,2-dibromides were treated with NaSPh. In this manner 1,2-bis(phenylthio)propane was obtained in 83% yield, b0.03 168°, from 1,2-dibromopropane, and 1,4-bis(phenylthio)-2-butene, m. 80°, in 93% yield from 1,4-dibromo-2-butene. Similar treatment of 1,2,3,4-tetrabromobutane gave olefin formation in the 2,3-position and substitution in the 1,4-position. Treatment of the 1-chloro-1-(ethylthio)acetophenone with NaSEt gave the 1,2-bis(ethylthio)-l,2-dibenzoylethane in 37% yield. Similar treatment of di-Et bromomalonate gave di-Et (ethylthio)malonate, b11 135-7°, and tetra-Et ethanetetracarboxylate, m. 76°. In the same way 2,2,3,3-tetracarbethoxybutane, n20D 1.4459 (55%), and di-Et methylmalonate, b. 83-6°, n20D – 1.4170 (34%), were obtained from di-Et methylbromomalonate. Analogous treatment of di-Et chloromalonate and di-Et dibromomalonate gave di-Et (ethylthio)malonate, b11 135°, 70% yield, tetra-Et ethylenetetracarboxylate, m. 56°, 55% yield. Tetracyanoethylene, m. 197°, was obtained in 36% yield from dibromomalononitrile-KBr complex; 1,1,2,2-tetracarbethoxycyclopropane, m. 42°, was obtained in 70% yield from 1,3-dibromo-1,1,3,3-tetracarbethoxypropane, and di-Et 1,2-bis(ethylthio)succinate, b0.1 117-35°, in 52% yield from the addition product of di-Et fumarate and EtSCl. 1,2-Bis(phenylthio)cyclohexane, b0.1 185-96°, was obtained in 49% yield by treatment of 2-chlorocyclohexyl Ph sulfide with NaSPh.
Rev. Chim., Acad. Rep. Populaire Roumaine published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C44H28ClFeN4, Category: bromides-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary