Oxacyclanes was written by Kirrmann, A.;Hamaide, N.. And the article was included in Bulletin de la Societe Chimique de France in 1957.Quality Control of 1-Bromo-6-methoxyhexane This article mentions the following:
Oxacyclanes were formed by heating 绾? 鏈? or 钄?methoxylated alkyl bromides with FeCl3. NaOMe (1 mole) in MeOH added slowly with stirring to 1 mole dibromoalkane at 60鎺? the mixture boiled gently 4 hrs. and cooled, the washed and dried product distilled, and the bromo methoxy alkane fraction carefully redistilled in vacuo gave MeO(CH2)6Br, b14 94鎺? nD20 1.458, d20 1.1942, MeCH(OMe)CH2CH2CHBrMe, b35 100鎺? nD20 1.441, d201.1824, MeO(CH2)5Br, b15 76鎺? nD20 1.455, d20 1.2420, and MeO(CH2)4Br (I), b15 60鎺? nD20 1.452, d20 1.3052, in 56, 53, 55, and 57% yields, resp. Regulated mild distillation of these products in the presence of a few mg. FeCl3 gave the oxacyclanes (compound, % yield, b.p., nD20, d20, 浣?in 娓?: tetrahydrofuran, 100, 67鎺? 1.407, 0.8874, 3.34, 6.85, 9.34; tetrahydropyran, 100, 88鎺? 1.4205, 0.8851, 3.30, 6.92, 9.12, 11.46, 12.26; hexamethylene oxide, 70, 116鎺? 1.4355, 0.895, 3.42, 6.90, 8.80, 9.02, 10.04, 10.30, 12.22, 12.44; 2,5-dimethyltetrahydrofuran, 80, 96鎺? 1.410, 0.8373, 3.3, 6.8, 7.2, 9.1, 11.3, 11.94, 12.1. The MeBr formed in the cyclization of I was condensed at -15鎺?with anhydrous Et2O and Mg, the MeMgBr treated with BzH and the MePhCHOH formed identified as the phenylurethan. The mechanism of the reaction was interpreted through the intermediary formation of a tertiary oxonium salt. In the experiment, the researchers used many compounds, for example, 1-Bromo-6-methoxyhexane (cas: 50592-87-5Quality Control of 1-Bromo-6-methoxyhexane).
1-Bromo-6-methoxyhexane (cas: 50592-87-5) belongs to organobromine compounds. A variety of minor organobromine compounds are found in nature, but none are biosynthesized or required by mammals. Organobromine compounds have fallen under increased scrutiny for their environmental impact. Many of the alkyl bromine derivatives are excellent alkylating agents since bromides are good leaving groups. Tribromides, like tetrabutylammonium tribromide, are used as a solid source of bromine. N-bromosuccimide (NBS) is used for the selective bromination of allylic bonds.Quality Control of 1-Bromo-6-methoxyhexane
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary