Nazarov, I. N. published the artcileStereochemistry of addition reactions at a triple bond. III. Stereochemistry of bromination of propargyl alcohols, HPLC of Formula: 594-81-0, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1960), 887-95, database is CAplus.
cf. CA 52, 3660g, 19925f. Photochem. bromination of HCCCH2OH (I) yielded trans-dibromide, while the tertiary acetylenic alcs. and acetates yielded mainly cis-dibromides. I and the calculated amount of Br in CCl4 added at 25° under ultraviolet light gave 74% 2,3-dibromo-2-propen-1-ol, b1 55-6°, m. 28-30°, whose trans structure was confirmed by infrared spectrum (shown). Bromination of dimethylethynylcarbinol in hexane under ultraviolet light gave 2,3-dibromo-2,3-dimethylbutane, m. 173-5°, and mainly a stereoisomeric mixture of dibromovinyldimethylcarbinols, b6 76-80°, nD20 1.5422, containing not over 8% trans isomer. Similar bromination of HCCCMe2OAc gave a little 2,3-dibromo-2,3-dimethylbutane, m. 172-5°, and 77% stereoisomers of AcOCMe2CBr:CHBr, b2 71-4.5°, nD21.5 1.5184, containing not over 11% trans isomer. Similar bromination in AcOH gave the above mixture, b10 80-103°, a fraction, b10 103-8°, nD20 1.4909 [which with semicarbazide gave bromoacetyldimethylcarbinyl acetate semicarbazone, m. 102-5° (CA 36, 7458)], and a polybromoketone, b3 91-106°, 1.5278. The mother liquors yielded with semicarbazide bromoacetyldimethylcarbinylsemicarbazide, m. 125-6°. cis-Dibromovinyldimethylcarbinyl acetate with MeONa-MeOH (loc. cit.) in the cold gave cis-dibromoethylene, containing not over 5% trans isomer, and mostly dimethylbromoethynylcarbinol, b17 68-70°; p-nitrobenzoate m. 88.5-9.5° (Straus, et al., CA 25, 71). The residues yielded some Me2C:CHCO2H. trans-CHBr: CBrCMe2OH with Ac2OH2SO4 in the cold gave mainly trans-3,4-dibromoisoprene and trans-CHBr:CBrCMe2OAc, b1 68-9°, 1.513-6, which with MeONa-MeOH gave trans-dibromoethylene and trans-CHBr:CBrCMe2OH. The latter and powd. KOH in Et2O in 2 hrs. at 35° gave 22% dibromoethylene, containing not over 16% cis form, along with unreacted material and some (CCMe2OH)2. Bromination of 1-ethynylcyclohexyl acetate in hexane under ultraviolet light gave 82% cis-1-(dibromovinyl)cyclohexyl acetate, b2.5 116-18°, nD19 1.5321. Similar bromination in AcOH at room temperature gave 60% 1-acetoxy-1-(dibromoacetyl)cyclohexanone, m. 51.5-2°, and mixed stereoisomers of 1-(dibromovinyl)cyclohexyl acetates, b1 101-4°, containing not over 13% cis-isomer. Keeping cis-1-(dibromovinyl)cyclohexyl acetate with alc. KOH 3 days gave 69% 1-bromoethynylcyclohexanol, m. 54.5-6°, and 13.5% cyclohexylideneacetic acid; S-benzylthiuronium salt m.162-3°. trans-1-(Dibromovinyl)cyclohexanol with Ac2OH3PO4 gave the corresponding acetate, b1.2 105.5-6°, nD20 1.5388. Ultraviolet irradiation of trans-dibromovinyldimethylcarbinol in hexane in the presence of a trace of Br 4 hrs. gave 81% cis-isomer; longer irradiation failed to increase this conversion. The trans-isomer kept 2 months in the dark yielded 69% cis-isomer. Irradiation of trans-(dibromovinyl)dimethylcarbinyl acetate gave also a mixture of cis-trans isomers containing 78% cis-form. The liquid trans-1-(dibromovinyl)cyclohexanol, illuminated in hexane solution, solidified and gave some 79% cis-isomer; keeping the trans-isomer 6 months in the cold gave 62% cis-isomer, m. 66-70°. The estimation of cis-trans isomers was done with the aid of infrared spectra, which were shown.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 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 C6H12Br2, HPLC of Formula: 594-81-0.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary