Category: 594-81-0

Streitwieser, Andrew Jr. published the artcileThe application of Taft’s equation to polar effects in solvolyses, Application In Synthesis of 594-81-0, the publication is Journal of the American Chemical Society (1956), 4935-8, database is CAplus.

The Taft equation, log (k/k₀) = σ*ρ* (cf. C.A. 48, 11888f), was applied to the solvolysis of secondary carbinyl sulfonates in AcOH, of tertiary halides in aqueous EtOH, and of primary tosylates in EtOH, with satisfactory results. Driving forces for anchimeric assistance are derived from the correlations.

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 C10H15ClO3S, Application In Synthesis of 594-81-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Sysoeva, N. D. published the artcileThe application of the Chugaev xanthic reaction to secondary-tertiary and ditertiary glycols. II. Experimental part. The effect of sodium xanthate on trimethylethylene dibromide, Safety of 2,3-Dibromo-2,3-dimethylbutane, the publication is Trudy Uzbekskogo Inst. Narodnogo Khoz. (1940), 1-11, database is CAplus.

The heating of the dibromides of the tri- and tetramethylethylenes with Na xanthate on a water bath at 60-70° resulted in the formation of tri- and tetramethylethylenes the separation and identification of which are described in detail. Through Khim. Referat. Zhur. 4, Number 7-8, 40-1(1941).

Trudy Uzbekskogo Inst. Narodnogo Khoz. 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 C12H15NO, Safety of 2,3-Dibromo-2,3-dimethylbutane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Miyagawa, Ichiro published the artcileStudies on internal rotation by the measurement of dipole moments. IV. The dipole moments of some halogenated hydrocarbons, Product Details of C6H12Br2, the publication is Nippon Kagaku Kaishi (1921-47) (1954), 1162-5, database is CAplus.

cf. C.A. 48, 13297h. The dipole moments of 2,3-dichloro-2,3-dimethylbutane, 2,3-dibromo-2,3-dimethylbutane, 1,2-dibromo-2-methylpropane, and 1,1,2-tribromoethane were measured in heptane at -20° to 50°. The energy difference between a trans and a gauche form and the moment of the gauche form were calculated The moment of 1,1,2-tribromoethane is independent of temperature The moment of this compound corresponds to that of the gauche form rather than to that of the C_s form.

Nippon Kagaku Kaishi (1921-47) 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, Product Details of C6H12Br2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Liu, Yu-Cheng published the artcileFree radical reaction. Reaction of Grignard reagents with 2-bromo-2,3-dimethylbutane and with 1-chloro-1-methylcyclohexane in the presence of cobaltous halides, Application In Synthesis of 594-81-0, the publication is Acta Chim. Sinica (1956), 104-11, database is CAplus.

cf. C.A. 51, 14569e. CHMe₂CBrMe₂ (I) decomp, when treated with PhMgBr (II) and CoBr₂ (III) to give 35% CHMe₂CHMe₂ (IV), 31% CHMe₂CMe:CH₂ (V), and 2% CMe₂:CMe₂ (VI). I (0.45 mole) added dropwise to 0.5 mole freshly prepared II in 250 ml. Et₂O containing III with stirring, stirred with cooling several hrs., the product poured into ice H₂O, 30 ml. AcOH added, the Et₂O layer separated, washed neutral, dried, and fractionally distilled to 80° gave 25.8 g. fraction, b. 53-8°, n²⁰_D 1.3822, containing some V (infrared spectrum), mainly IV as shown by oxidation with O₃ in CCl₄ at 0° to CH₂O (IV derivative with saturated 5,5-dimethyldihydroresorcinol, m. 192-3°) and some Me₂CHCOMe; 2,4-(O₂N)₂C₆H₃NHNH₂ derivative, m. 114-15°. The fraction b. 71.5° (0.7 g.) proved to be VI, m. 165° (sublimation). The residue gave 33 g. biphenyl, m. 70-2°, on steam-distillation Treatment of 9.7 g. I with 11.2 g. KOH in 50 ml. glycol at 100-10° 1.5 hrs. gave 4.1 g. distillate, n²⁰_D 1.4076, a mixture of 79% VI and 21% V. Bromination of 0.5 g. of this mixture in CCl₄ yielded 61% CBrMe₂CBrMe₂, m. 170-5°. 1-Methylcyclohexyl chloride (VII) (0.2 mole) in 100 ml. absolute Et₂O added dropwise to 0.3 moles MeMgBr (VIII) in 320 ml. Et₂O with frequent addition (6.5 g. total) of III and stirring continued an addnl. hr. after complete evolution of the gas gave as the main distillate, b. 100-3°, n²⁰_D 1.4371, 62% mixture of C₆H₁₁Me, 1-methylcyclohexene (IX), and methylenecyclohexane. The % unsaturation of bromate-bromide titration and catalytic hydrogenation with Pt was 51, infrared absorption spectrum showed the presence of C:CH, and group oxidation with O₃ gave cyclohexanone; 2,4-dinitrophenylhydrazone, m. 158.5-9.5°. VII (26.5 g.) in 40 ml. absolute Et₂O with 0.4 mole iso-PrMgBr in 200 ml. Et₂O in the presence of 2.6 g. III in the same way as above gave 11.3 g. distillate, b. 100-3°, n²⁰_D 1.4348, % unsaturation = 42, a mixture of the same products as from VII and VIII. VII (5 g.) and 25 ml. 4N NaOH refluxed on a steam-bath 3 hrs., extracted with Et₂O, and distilled, gave 2.4 g. IX, b. 107-8°, n²⁰_D 1.4364. It is therefore suggested the disproportionation of alkyl radicals in solution is probably a bimol. reaction and the number of α-H atoms has a directive influence upon the orientation of olefin formation.

Acta Chim. Sinica 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, Application In Synthesis of 594-81-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Kuivila, Henry G. published the artcileOrganotin hydrides and organic free radicals, SDS of cas: 594-81-0, the publication is Accounts of Chemical Research (1968), 1(10), 299-305, database is CAplus.

The preparation and properties of organotin hydrides, their reduction of alkyl and aryl halides, aldehydes, ketones, isocyanates, and isothiocyanates and their addition to C-C double or triple bonds, their use in the study of organic free radicals, i.e. octen-5-yl free radicals, cyclization of unsaturated acyclic radicals, the tritylmethyl radical, free-radical β-eliminations, vinyl free radicals and photoreduction, are reviewed with 39 references.

Accounts of Chemical Research 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, SDS of cas: 594-81-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Anderson, J. E. published the artcileIntrinsic asymmetry. Its effect on the chemical shift of groups which are not diastereotopic, SDS of cas: 594-81-0, the publication is Tetrahedron (1976), 32(22), 2789-93, database is CAplus.

The effect was determined of intrinsic asym. on the chem. shifts of Me2CRCMe2R1 (R = H, R1 = Cl, Br, I; R1 = R2 = Cl, Br, I, CN, Ph, 3-ClC6H3, Et, Me3CCH2; R = I, R1 = 4-MeOC6H4), in which rotation is slow on the NMR timescale. When R = R1 = alkyl or diamagnetically anisotropic Ph groups the intrinsic asym. shifts are very small. When either R or R1 is a halogen atom substantial intrinsic asym. shifts were observed; I > Br > Cl. The effect of 2 C-halogen bonds compared with one C-halogen and one C-H bond is inconsistent; 2 C-Cl bonds gave no shift, 2 C-Br bonds gave a reduced shift, and 2 C-I bonds gave an enhanced shift. The effect is tentatively linked to bond polarizability.

Tetrahedron 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, SDS of cas: 594-81-0.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bergmann, A. G. published the artcileReactions of combination with conjugated systems of double linkings. II. Combination of hydrogen bromide with di-isopropenyl [β,γ-dimethyl-Δ^αγ-butadiene], Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane, the publication is Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1920), 37-40, database is CAplus.

The combination of HBr with β,γ-dimethyl-Δ^αγ-butadiene in glacial AcOH takes place in the 2 stages: (1) CH₂:CMeCMe:CH₂ + HBr = CMe₂BrCMe:CH₂, and (2) the latter + HBr = CMe₂BrCMe₂Br (30%) + CMe₂BrCHMeCH₂Br (70%). γ-Bromo-β,γ-dimethyl-Δ^α-butene, C₆H₁₁Br, b₁₀₀ 84-6°, d₂₀ 1.2201, yields dimethylisopropenylcarbinol when hydrolyzed by means of aqueous KOH. β,γ-Dibromo-β,γ-dimethylbutane was described by Thiele (Ber. 27, 454). α,γ-Dibromo-β,γ-dimethylbutane is a liquid, b_16.5 88-9°, d₂₀ 1.6065. The product of the union of 1 mol. of HBr with isoprene, viz., γ-bromo-γ-methyl-Δ^α-butene, combines with a 2nd mol. of HBr, apparently giving only βδ-dibromo-β-methylbutane.

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva 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, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bogonostseva, N. P. published the artcileReaction of some halogen derivatives with sodium diethyl phosphite, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane, the publication is Uchenye Zapiski, Kazan. Gosudarst. Univ. im. V. I. Ul’yanova-Lenina (1956), 116(No. 2), 71-128, database is CAplus.

Ph₂CHBr (10 g.) in Et₂O-C₆H₆ with (EtO)₂PONa from 5.35 g. ester and 0.9 g. Na gave NaBr and 61.33% (Ph₂CH)₂ and 5.3 g. unidentified yellow liquid Ph₂CHCl and (EtO)₂PONa did not react in Et₂O; in iso-Am₂O a little NaCl formed; in MePh a reaction took place after 2 h. reflux yielding a little Ph₂CHOH, (Ph₂CH)₂O, and 21% Ph₂CHP(O)(OEt)₂, b₄ 184-8°, d₀²⁰ 1.1277, n_D²⁰ 1.5460, m. 38-40°; the latter hydrolyzed with 10% HCl to the free acid, m. 223-5° (from H₂O); the same ester formed in 43.65% yield from (EtO)₃P with Ph₂CHBr in Et₂O; the ester, b₂ 180-1°, d₀²⁰ 1.1287, n_D²⁰ 1.5445, m. 39-40°, which hydrolyzed with 10% HCl at 150-80° to the free acid, m. 227-8°. (EtO)₂PONa in Et₂O with PhCH₂Cl readily gave 49.35% PhCH₂PO(OEt)₂ (I), b₁₁ 153-4°, d₀⁰ 1.1200, n_D²⁰ 1.4965, which hydrolyzed with 10% HCl to the free acid, m. 169-70°. Similarly, PhCH₂Br gave 44% I, b₁₂ 153-5°, d₀⁰ 1.1189, n_D²⁰ 1.4892, while PhCH₂I gave 21.1% I. To (EtO)₂PONa from 2.5 g. ester and 0.32 g. Na in Et₂O was added Ph₂CBrCCl₃ in Et₂O and after refluxing 2 h. there was obtained 1.9 g. NaBr, 32.05% (Ph₂CCCl₃)₂ (II), a glassy solid, b₃ 180-90°, and a range of products, b₈ 60° to b₃ 160°, which contain P; a substance C₁₀H₁₄O₃ClP, b₃ 154-60°, n_D²⁰ 1.5010, d₂₀²⁰ 1.2332, was isolated but not identified. Heating 8 g. (EtO)₃P with 15.4 g. Ph₂CBrCCl₃ to 155-60° 2 h. gave 42.4% II and some low-boiling material. Refluxing (EtO)₂PONa in Et₂O with Ph₂CClCCl₃ 6 h. gave NaCl and much unreacted halide; a similar reaction in dioxane in a sealed tube at 130-50° gave in 7 h. unreacted halide and Ph₂C:CCl₂. Ph₂CClCCl₃ (5 g.) and 3 g. (EtO)₈P refluxed 3 h. gave unreacted halide, Ph₂C:CCl₂, and no P-containing substance. Ph₂C:CH₂ with HBr gave crude Ph₂CBrMe, 10 g. of which with (EtO)₂PONa from 7.5 g. ester and 1.2 g. Na in Et₂O gave after refluxing 4 h. 6.35 g. NaBr, 6.9% Ph₂C:CH₂, and a crude substance, b_2.5 168-85°, which contains P. Ph₂CBrMe (5.05 g.) with 3.2 g. (EtO)₃P gave in 5 h. reflux EtBr and 44.9% crude Ph₂C:CH₂. Crude Ph₂CClMe (prepared from the olefin and HCl) with (EtO)₂PONa in Et₂O gave, after 3 h. reflux, NaCl and Ph₂C:CH₂; Ph₂CClMe with (EtO)₃P refluxed 3 h. gave mainly Ph₂C:CH₂. No appreciable reaction took place between (EtO)₂PONa and (1-C₁₀H₇)₂CHBr in Et₂O; the result was the same with (EtO)₃P in 2 h. at 200°; the same result was obtained with (1-C₁₀H₇)₂CHCl and (EtO)₂PONa in Et₂O, or in dioxane at 130-40°. Only slight reaction took place between (EtO)₂PONa and 9-bromofluorene in Et₂O; the latter with (EtO)₃P in 6 h. at 260° gave no EtBr and no reaction could be detected. 9-Chlorofluorene failed to react with (EtO)₂PONa or (EtO)₃P. 2-Bromocyclohexanone with (EtO)₂PONa in Et₂O gave 31% di-Et cyclohexanone-2-phosphonate, b_11.5 148-9, d₀⁰ 1.1270, n_D²⁰ 1.4578, which gave no definite products after hydrolysis with 10% HCl; similarly, 2-chlorocyclohexanone gave 35% above ester, b_11.5 151.5-3°, d₀⁰ 1.1380, n_D²⁰ 1.4518, which again failed to yield definite products after hydrolysis with HCl. 2-Chlorocyclohexanone with (EtO)₃P after 2 h. at 110-20° gave 54.5% above ester; hydrolysis of this with HCl gave some cyclohexanone and H₃PO₄. Bz₂CHBr with (EtO)₂PONa in Et₂O gave NaBr and 69.1% Bz₂CH₂; the same reaction in C₆H₆ gave 42.7% Bz₂CH₂, while 82.3% NaBr was isolated. Bz₂CHBr with (EtO)₃P gave 60.8% Bz₂CH₂. Bz₃CBr with (EtO)₂PONa in Et₂O gave 58.3% Bz₃CH, some Bz₂CH₂, and a substance, b₈ 90-1°, identified as (EtO)₃PO. Bz₃CBr with (EtO)₃P gave 56.6% Bz₃CH, and (EtO)₃PO. Bz₂CHBr in MePh with Na gave Bz₂CH₂ and some Bz₄C₂H₂; Na and Bz₃CBr in MePh gave a trace of Bz₃CH and unreacted halide. (EtO)₂PONa with o-C₆H₄(CO)₂CBrCO₂Et gave indanedione and some diphthalylethane, decompose 215°; (EtO)₃P gave the same products. o-C₆H₄(CO)₂CNaCO₂Et with (EtO)₂POCl in Et₂O gave diphthalylethane and indanedione. Bromoindanedione and (EtO)₂PONa gave diphthalylethane; (EtO)₃P gave indanedione. Bromoindanedione and Na in MePh gave indanedione. (EtO)₂PONa (from 15.85 g. ester) and 14 g. (Me₂CBr)₂ in Et₂O reacted completely in 7 min. yielding 60% (Me₂C:)₂ and unidentified material, b₄ 60-70°, which reacts with Na. 9,10-Phenanthrenedibromide and (EtO)₂PONa in Et₂O gave phenanthrene and (EtO)₂POH, and unidentified material, b₉₀ 110°, which on hydrolysis gave H₃PO₄. Dibromophenanthrene and (EtO)₃P gave phenanthrene and (EtO)₂POH. (EtO)₂PONa (from 26.6 g. ester) with 24.6 g. (CH₂OCH₂CH₂Br)₂ on 2 days standing gave 14.7% (CH₂OCH₂CH₂PO₃Et₂)₂, b₂ 228-9°, d₂₀²⁰ 1.1416, n_D²⁰ 1.4478, which with HCl hydrolyzed to an uncrystallizable free acid, which was analyzed as the Ba salt. (CH₂OCH₂CH₂Br)₂ with (EtO)₃P gave impure ester identical with that above but decomposing on distillation (EtO)₂PONa (from 33 g. ester) with 25.7 g. Br(CH₂)₄Br gave 61% (CH₂CH₂PO₃Et₂)₂, b₇ 214-17°, d₂₀²⁰ 1.1173, n_D²⁰ 1.4460, decompose on boiling; hydrolysis gave an uncrystallizable oil. (CH₂)₄Br₂ (10 g.) with 15.5 g. (EtO)₃P gave 58.4% above ester, b₈ 215-16°, d₂₀²⁰ 1.1176, n_D²⁰ 1.4495. (EtO)₂PONa (from 19.2 g. ester) with 30 g. 1-iodo-2-ethoxy-3-butene refluxed 1 h. in Et₂O gave 33.5% crude, or 17% pure, CH₂:CHCH(OEt)CH₂PO(OEt)₂, b₇ 119-20°, d₀⁰ 1.0409, n_D²⁰ 1.4231, and much polymerized undistillable matter; the same ester formed in 30% yield in a larger experiment The iodide with (EtO)₃P refluxed 2 h. yielded 30% same ester as above. (EtO)₂PONa with 1-chloro-2-ethoxy-3-butene gave NaCl and liquid material which decomposed extensively on attempted distillation and much polymeric matter; the chloride and (EtO)₃P gave much unreacted material and a little substance, b_4.5 124-6°, d₀⁰ 1.0592, n_D²⁰ 1.4495, containing 14-14.5% P. (EtO)₂PONa with 1-chloro-4-ethoxy-2-butene gave NaCl, unreacted halide, MePO(OEt)₂ (uncertain), and material, b₃ to 205°, which analyzed as C₅H₁₃O₃P to C₁₈H₄₁O₁₀P₃. 1-Chloro-4-ethoxy-2-butene with (EtO)₃P gave a little substance, b_4-6 136-42°, with much decomposition The nature of the products is unknown.

Uchenye Zapiski, Kazan. Gosudarst. Univ. im. V. I. Ul’yanova-Lenina 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, Recommanded Product: 2,3-Dibromo-2,3-dimethylbutane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Sergienko, S. R. published the artcileTransformations of diene compounds in the presence of oxide catalysts. Transformations of 2,3-dimethyl-1,3-butadiene on aluminosilicate, Safety of 2,3-Dibromo-2,3-dimethylbutane, the publication is Doklady Akademii Nauk SSSR (1953), 803-6, database is CAplus.

cf. C.A. 48, 11290g. Passage of 2,3-dimethyl-1,3-butadiene over pelleted aluminosilicate at 250° (at 200° little reaction takes place, while above 250° much decomposition occurs) gave 7-10% C₅-hydrocarbons and 35-40% dimeric products, the remainder being trimers and higher condensation products. The identified products were 2,3-dimethyl-2-butene, 2,3-dimethylbutane, apparently cyclic dimers, b. 187-95°, and higher products. The fresh catalyst is gradually coated not with C but with a hydrocarbon C_nH_2n-18, a resinous solid, the composition of which was between a pentamer and a hexamer of the diene.

Doklady Akademii Nauk SSSR 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 C3H8N2S, Safety of 2,3-Dibromo-2,3-dimethylbutane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Tzerpos, Nikolaos I. published the artcileDiphenylpyridylmethyl radicals. Part 1. Synthesis, dimerization and ENDOR spectroscopy of diphenyl(2-, 3- or 4-pyridyl)methyl radicals; bond dissociation enthalpies of their dimers, Formula: C6H12Br2, the publication is Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1995), 755-61, database is CAplus.

Ortho-ortho hydrogen van der Waals repulsions are the origin of the propeller shape of the triphenylmethyl radical and the main reason for the low bond dissociation enthalpy (BDH) of its dimer I (44.8 J mol^-1). In order to reduce these steric repulsions (eliminating some aromatic hydrogens), diphenyl(2-, 3- or 4-pyridyl)methyl radicals (e.g, II) were prepared through reductive dehalogenation of the corresponding triarylchloromethanes (e.g., III) with silver in benzene. They form α,p-dimers IV–VI exclusively through the pyridine ring. ENDOR spectroscopy shows that the structure of the radicals, does not deviate substantially from that of the parent radical, Ph₃C•. In contrast, the BDH values of the dimers (measured using ESR spectroscopy) show strengthening of the central C-C bond in IV (88.7 kJ mol^-1) and V (90.0 kJ mol^-1) and a similar value for VI (46.4 kJ mol^-1) with respect to the trityl dimer I. This is a consequence of the ground state stabilization of the dimers IV–VI due to relief of strain (elimination of ring hydrogens), whereas in the case of VI, this stabilization is probably compensated by the formation of a weaker C-N bond with respect to the C-C bond. The above dimers undergo easy 1,5-H-rearrangement, autocatalyzed by the basic pyridyl groups themselves.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry 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 C11H24O3, Formula: C6H12Br2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary