Yamato, Takehiko published the artcileMedium-sized cyclophanes. Part 57. Synthesis, conformations and stereodynamics of [2.n]metacyclophan-1-enes and their conversion to [2.n]metacyclophan-1-ynes, Application In Synthesis of 111865-47-5, the publication is New Journal of Chemistry (2001), 25(5), 728-736, database is CAplus.
Anti- and syn-[2.8]Metacyclophan-1-enes I, which are both conformationally rigid structures, were prepared in good yields by a McMurry cyclization of 1,8-bis(5-tert-butyl-3-formyl-2-methoxyphenyl)octane. Similarly, McMurry cyclization of 1,10-bis(5-tert-butyl-2-methoxy-3-formylphenyl)decane afforded (E)- and (Z)-[2.10]-metacyclophan-1-enes II in good yields. The assignment of the E and Z structures was confirmed by 1H-NMR analyses and single crystal X-ray diffraction studies. Bromination of (E)- and (Z)-II with benzyltrimethyl- ammonium tribromide affords exclusively the cis-adduct to the bridged double bond. When treated with potassium tert-butoxide in refluxing tert-BuOH at 80°C for 3 h, the bromine meso adduct gave the dehydrobrominated product [2.10]metacyclophan-1-yne in 93% yield, along with a 1-bromo[2.10]metacyclophan-1-ene in 7% yield; the same reaction with the dl-bromine adduct from II gave 29% of [2.10]metacyclophan-1-yne along with 71% of the 1-bromo[2.10]metacyclophan-1-ene. Similarly, anti- and syn-[2.8]metacyclophan-1-ynes were also prepared by bromination of syn-[2.n]metacyclophan-1-ene syn-I, followed by the dehydrobromination of the bromine adduct. The characterization and the reaction pathway of these products are discussed. The dynamics of the ring inversion and UV spectra are also presented.
New Journal of Chemistry published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C5H8N2O, Application In Synthesis of 111865-47-5.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary