The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ferrocene and related organometallic π-complexes. IV. Some Ullmann reactions of haloferrocenes》. Authors are Rausch, Marvin D..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Product Details of 1273-73-0. Through the article, more information about this compound (cas:1273-73-0) is conveyed.
cf. CA 54, 22540e. Haloferrocenes were found to undergo the Ullmann coupling reaction readily. Iodoferrocene (I) and Cu bronze form biferrocenyl (II) in quant. yield at 150°. Both I and 1-iodo-2-nitrobenzene (III) formed coupling products in 95-100% yield at temperatures as low as 60°. A series of ferrocenyl aryl ethers were prepared by the Ullmann condensation of I and K aryloxides. I was prepared in 60-70% yield by the reaction of chloromercuriferrocene and iodine in xylene at 75-80°, m. 49-9.5° (MeOH-H2O). Bromo- (IV) and chloroferrocene (V) were obtained by the reaction of ferrocenylboronic acid with CuBr and CuCl, resp. I (0.936 g.) and 1.9 g. Cu bronze heated 16 hrs. at 140-50°, the mixture extracted with hot C6H6, and the extract evaporated gave 0.510 g. II, m. 239-40° (decomposition). In experiments in which less pure I was used the yield of II was appreciably less than quant. Similar reactions in which I was replaced by IV and V gave yields of 97 and 65% II, resp. I (0.405 g.), 0.83 g. Cu bronze, and 4 g. biphenyl heated 16 hrs. at 130°, and then 3 hrs. at 158-60°, and the residues chromatographed gave a total of 76% II. Reactions in which HCONMe2 was used as solvent and diluent gave mostly ferrocene. When the reaction was carried out using Zn and heating 19 hrs. at 150° and the product chromatographed on Al2O3, 17% II was obtained. II was less soluble in common organic solvents than ferrocene. The infrared and ultraviolet spectra of II were discussed. III (4.98 g.) and 12.7 g. Cu bronze heated 60 hrs. at 60° gave 2.3 g. 2,2′-dinitrobiphenyl, m. 125°. Similarly, 4.98 g. 1,3-I(O2N)C6H4 and 12.7 g. Cu bronze afforded a crude product which when chromatographed on Al2O3 gave 1% 3,3′-dinitrobiphenyl, m. 197-8°, and 4.20 g. unchanged material. In a reaction similar to that described above 20.4 g. PhI and 1 g. Cu bronze gave 16 g. unchanged PhI and no trace of Ph2. I (0.624 g.) and 1.28 g. Cu bronze gave 97% II. I (0.405 g.), 0.324 g. III, and 1.65 g. Cu bronze gave a crude product which when chromatographed on Al2O3 gave 71% II, and 7.5% 2-nitrophenylferrocene, m. 116-17°. Ferrocenyl aryl ethers were prepared by the following typical procedure. 2-Naphthol (1.44 g.) and 0.28 g. KOH heated at 150° until all the KOH dissolved, 0.936 g. I and 0.02 g. Cu bronze added, the mixture heated 16 hrs. at 115°, cooled, the contents washed with 10% KOH, extracted with refluxing C6H6, and the product chromatographed on Al2O3 gave 0.11 g. ferrocene and 0.12 g. ferrocenyl 2-naphthyl ether, m. 143-3.5° (heptane). The following further ferrocenyl aryl ethers were prepared (aryl group, m.p., and % yield given): Ph, 93-3.5°, 28; 3-(3-phenoxyphenoxy)phenyl, 74-4.5°, 50; 2-biphenylyl, 141-2°, 62; 4-BrC6H4, 87-7.5°, 22. All ferrocenyl aryl ethers exhibited strong absorption in the 1270-1230 cm.-1 region. When heated in sealed capillaries the ethers did not appear to decompose
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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com