General Description
1,3-Dibromoadamantane is reported to react with diphenylphosphide ions (Ph
2P
-) under photostimulation by the S
RN1 mechanism. The viscosity-dependent retarding effect of 1,3-dibromoadamantane in highly viscous polymeric chlorotrifluoroethene has been studied by 13C NMR relaxation measurements. Preparation of 1,3-dibromoadamantane via dibromination of adamantine has been reported.
Synthesis
Reactions were carried out in 20 mL glass ampoules or 17 mL stainless steel pressure microreactors with consistent results from parallel experiments. Under argon protection, 0.3 mmol of tris(acetylacetonato)iron(III) [Fe(acac)3], 10 mmol of adamantane, 10 mmol of carbon tetrabromide (CBr4), and 150 mmol of dibromomethane (CH2Br2) were added to the microreactor (or ampoule). The reactor (or ampoule) was sealed and heated under stirring conditions. After completion of the reaction, the reactor (or ampoule) was cooled to room temperature, opened and the solvent was removed by distillation and the residue was purified by crystallization with hexane or ethanol. The conversion of adamantane and the yield of its derivatives were determined by gas chromatography (GLC) using decene as an internal standard with correction factors of 1.09 and 1.53 for adamantane and bromoadamantane, respectively.The structures of the resulting compounds were confirmed by comparison with known samples and literature data.
References
[1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 2, p. 184 - 187
[2] Zh. Org. Khim., 2015, vol. 51, # 2, p. 196 - 199
[3] Tetrahedron Letters, 1986, vol. 27, # 12, p. 1399 - 1402
[4] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2041
[5] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 10, p. 2239 - 2240
