Traynham, J. G. published the artcileEffects of ring size on the reactions of cyclic olefins. Halohydrins from methylene cycloalkanes, Name: 2-Bromo-2-methylpropan-1-ol, the publication is Tetrahedron (1959), 165-72, database is CAplus.
cf. C.A. 51, 12835c. Addition of HOCl to methylene cycloalkanes, (CH2)n.C:CH2 (I) (n = 3-6) gave mixtures of (CH2)n.C(OH)CH2Cl (II) and (CH2)n.CClCH2OH (III) with III predominating with n = 3 or 5. Addition of HOBr to I gave only (BrCH2OH (IV) together with (HCHO (V) in amounts dependent on n. The appropriate 1-chloro-1-(chloromethyl)cycloalkane and an approx. equimolar amount of CaCO3 in H2O refluxed 6 hrs. gave 28-39% yields of authentic II. II with aqueous KOH gave the corresponding methylenecycloalkane oxide (VI), (H2 (n, b.p./mm., nD30, and MR found given): 3, 90-2°/760, 1.4207, -; 4, 43-4°/62, 1.4290, 27.4; 5, 62-3°/37, 1.4470, -; 6, 84-5°/40, 1.4552, 36.5. VI (0.01-0.06 mole) dripped into 20 ml. concentrated HCl at below 5° and stirred 1 hr., poured onto ice, and the product extracted gave poor yields of III, giving immediate precipitates with alc. AgNO3, but none with NaI in Me2CO, reducing KMnO4, giving neg. tests with Lucas reagent, showing no infrared absorption near 7.25 μ. VI treated with chilled 48% HBr and the mixture stirred 1 hr., neutralized with solid Na2CO3 and extracted with Et2O, the washed and dried extract evaporated, and the residue distilled gave IV, forming an immediate precipitate with alc. AgNO3, and giving neg. tests with Lucas reagent and with NaI in Me2CO. IV (n = 4, 5, 6) refluxed 5-6 hrs. with 5M HCl gave good yields of V [n, b.p./mm., nD20, d20, m.p. of semicarbazone (or 2,4-dinitrophenylhydrazone) given]: 4, 55-6°/36, 1.4343, 0.920, 123-4°; 5, 49.5°/10, 1.4490, 0.930, – (172-3°); 6, 45.5-46°/4, 1.4621, -, 154-5°. Except for preparation from VI (n = 3), the initial product mixtures contained appreciable amounts of V, estimated by infrared determination of the composition of the Et2O extract residue, confirmed by fractional distillation (n, total % yield from HBr and VI, % IV and % V given): 4, 45, 65, 35; 5, 68, 95, 5; 7, 87, 68, 32. Cl and Br added with stirring to chilled aqueous suspensions of HgO and Ag2SO4, resp., and the approx. 1.8M solutions distilled at 40° in vacuo in the dark gave HOCl and HOBr solutions (exact. concentrations determined iodometrically). I (0.12 mole) in 200 ml. H2O was stirred below 15° with addition of 20% excess cold HOCl or HOBr until the mixture no longer turned acidified starch-iodide paper blue and the process repeated until all acid solution was added, the mixture stirred 1 hr. and saturated with NaCl, the aqueous layer extracted with Et2O and the combined organic product fractionated through a Vigreux column, the product components identified by comparison with authentic samples, and the product distributions estimated by comparison with known mixtures and results of fractional distillation Me3CH (0.16 mole) with HOBr yielded 77% product containing 97% Me2C(CH2Br)OH, b31 66-6.5°, nD20 1.4722, d20 1.451, and not more than 3% Me2CBr-CH2OH. The product distributions in hypohalous acid additions to I were tabulated (n, total % yield with HOCl, % III, % II, total % yield with HOBr, % IV and % V given): 3, 72, 60, 40, 78, 99, -; 4, 64, 41, 58, 67, 91, -; 5, 92, 67, 32, 89, 98, 2; 6, 86, 35, 64, 87, 87, 13. The phys. properties of authentic halohydrins were tabulated (halohydrin, n, b.p./mm., d20, and nD20 given): II, 3, 56-60°/20, 1.135, 1.4688; III, 3, 69-70°/20, 1.154, 1.4760; II, 4, 57-8°/6, 1.143, 1.4841; III, 4, 62-3°/3, 1.182, 1.5036; II, 5, 54-5°/4, 1.127, 1.5024; III, 5, 53-4°/2, 1.113, 1.4905; II, 6, 56-8°/2, 1.118, 1.4997; III, 6, 70-1°/2, 1.128, 1.5114; IV, 3, 64-5°/10, 1.506, 1.5041; IV, 4, 45-6°/2, 1.463, 1.5126; IV, 5, 55-6°/2, – (m. 82.3°), -; IV, 6, 73-4°/3, 1.339, 1.5232. The results were discussed and an interpretation included.
Tetrahedron published new progress about 55376-31-3. 55376-31-3 belongs to alcohols-buliding-blocks, auxiliary class Polymerization Reagents,ATRP Initiators, name is 2-Bromo-2-methylpropan-1-ol, and the molecular formula is C18H28B2O4, Name: 2-Bromo-2-methylpropan-1-ol.
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