Journal of the American Chemical Society 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 C17H37NO3, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane.
Sweeting, Orville J. published the artcile1,3-Dienes. II. Stereoisomerism of bromides and glycols derived from 2,3-dimethyl-1,3-butadiene, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane, the publication is Journal of the American Chemical Society (1946), 1057-61, database is CAplus.
cf. C.A. 35, 1377.4. (MeC:CH2)2 (I) (41 g.) in 200 mL. CHCl3 at -10°, treated with 80 g. Br in 150 mL. CHCl3 during 5 h., gives 87% of the trans-1,4-dibromide (II), b5 88.5-91.5°, m. 47-7.5°, and small quantities of the cis-isomer (III), b5 77.5-9.5°, d425 1.6695, nD25 1.5558, nD50 1.5420, and of the 1,2,3,4-tetrabromide (IV), m. 138.5-9°. I (76 g.) in 200 mL. petr. ether at -5°, treated with 148 g. Br at such a rate that the temperature remained below 0° (7 h.), gives 25.5 g. of IV, 75% of II, and 4% of III. When the reaction of I and Br in CHCl3 is illuminated with UV light (temperature not above 30°) there result 10% of II and 46% of III; without illumination, 80% of II was formed. Ozonolysis of III gives 75% of BrCH2Ac; no HCHO was found. II (25 g.), heated under reduced pressure at 120° for 15 h., gives 11.1 g. of III. II (65 g.) and 60 g. AcOK in 550 mL. absolute EtOH, refluxed 10 h., give 67% of trans-1,4-diacetoxy-2,3-dimethyl-2-butene (V), m. 38.5-9°; similarly, III gives 75% of the cis-isomer (VI) of V, b7 108-11°, b28 138-44°. V (5 g.) in 100 mL. CCl4, treated with 4 g. Br at -10°, gives 17% of the 2,3-di-Br derivative, b7 70-2°, which rapidly becomes green and then black; the same compound appears to be formed from VI, and also by stirring 15 g. of IV and 25 g. AcOAg in AcOH for 14 h. IV does not react with AcOK. V (10 g.) and 31.5 g. Ba(OH)2 in 50 mL. EtOH, refluxed and stirred for 5 h., give 46% of trans-2,3-dimethyl-2-butene-1,4-diol (VII), m. 57-8° (bisphenylurethane, m. 157-7.5°); the cis-isomer (VIII), b5 110-15° (bisphenylurethane, m. 147-8°). Pinacol and aqueous HBr give 2,3-dibromo-2,3-dimethylbutane, m. 177-7.5° (sealed tube). The following values for μ × 1018 are given: II 1.72, III 2.49, IV 1.55, V 1.90, VI 2.58, VII 1.93, VIII 2.52, and trans-1,4-dibromo-2-butene 1.63. The phys. and chem. evidence affords reasonable grounds for assigning the trans-configuration to II, V, and VII. All the evidence is consistent with the view that III is the cis-isomer and that VI and VIII are largely, if not entirely, the cis-isomers.
Journal of the American Chemical Society 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 C17H37NO3, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary