The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reaction of N-bromosuccinimide with nitriles. II. Aliphatic nitriles》. Authors are Couvreur, P.; Bruylants, A..The article about the compound:2-Bromopropanenitrilecas:19481-82-4,SMILESS:CC(Br)C#N).Electric Literature of C3H4BrN. Through the article, more information about this compound (cas:19481-82-4) is conveyed.
cf. C.A. 44, 7223d. A study of the reaction of (CH2CO)2NBr (I) with normal saturated nitriles, carried out on a series of 5 homologs, showed that the α-brominated derivatives predominated; the β-isomers were found only in small yield at best, even when Bz2O2 was used as a catalyst. MeCN, I, and 10% Bz2O2 in CCl4 refluxed 51 h. did not react; S as catalyst gave a complete reaction in 14 h. and 12% BrCH2CN. In 24 h. 0.5 mol each EtCN and I with Bz2O2 in CCl4 gave 5.2% MeCHBrCN, b50 68-9°, d15 1.5673, d30 1.5433, n15D 1.4673, n30D 1.4604, converted by concentrated H2SO4 to MeCHBrCONH2, m. 123°, and 46.8% product (probably MeCBr2CN), b12 87-8°, d15 2.2836, d20 2.2563, n15D 1.5636, n30D 1.5570, becomes yellow after 15 min. in light. Refluxing 0.75 mol EtCN, 0.5 mol I, Bz2O2, and no solvent 11 h. gave 45% MeCHBrCN. Me2CBrCN (80% from 1.5 mol Me2CHCN, 1 mol I, 10% Bz2O2 and no solvent in 90 min.), b50 60-3°, converted to Me2CBrCONH2, m. 144-5°; a similar yield was obtained in 6.5 h. with no catalyst. PrCN (1.5 mol), 1 mol I, and 10% Bz2O2 in 3 h. gave 47% EtCHBrCN, b20 63-5°, n20D 1.4652, converted by concentrated H2SO4 to EtCHBrCO2H, m. 110-11°, and 24% EtCHBrCN, b10 69-73°, n20D 1.4754 (amide, m. 95-6°, losing HBr readily). In 30 min. 1.5 mol BuCN, 1 mol I and 10% Bz2O2 gave 11.4% PrCHBrCN, b10 67° (amide m. 78-9°, and 26.6% product, probably MeCHBr(CH2)2CN, b10 91-2.5°, d15 1.4142, d30 1.3965, n15D 1.4777, n30D 1.4718, MRD 32.15. The latter compound on acid hydrolysis gave a subst. which was not the known EtCHBrCH2CO2H.
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Highly efficient and robust molecular ruthenium catalysts for water oxidation,
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