The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reduction of pentaerythrityl tetrabromide in ethanol with zinc. Isolation of spiropentane》. Authors are Slabey, Vernon A..The article about the compound:Pentaerythrityltetrabromidecas:3229-00-3,SMILESS:BrCC(CBr)(CBr)CBr).Application of 3229-00-3. Through the article, more information about this compound (cas:3229-00-3) is conveyed.
Pentaerythrityl tetrabromide (1940 g.), added in small portions (4 hrs.) to a refluxing mixture of 2500 ml. EtOH, 875 ml. H2O, 1300 g. Zn dust, 530 g. Na2CO3, and 125 g. NaI, the mixture boiled an addnl. hr., and the distillate fractionated through a 22-mm. glass column, 7 ft. in length, packed with 3/32-in. single-turn glass helices (rated as 100 theoretical plates at total reflux), gives 78-89% of a mixture containing 56% of methylenecyclobutane (I), f.p. -134.68°, b760 42.22°, nD20 1.42087, d420 0.7401; 26% of spiropentane (II), f.p. -107.05°, b760 39.03°, nD20 1.41220, d420 0.7551; 15% of 2-methyl-1-butene (III), f.p. -137.50°, b760 31.12°, nD20 1.37781, d420 0.6504; and 1-3% of dimethylcyclopropane. The method of Murray and Stevenson (use of molten AcNH2, C.A. 38, 1476.9, 3615.1) gave a total hydrocarbon yield of only 37-8% (36-10% I, 47-60% II, and 17-30% III).
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Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem