70680-23-8Relevant articles and documents
Helically chiral thia- and diselena-quinquephenylophanes
Airola, Karri,Bartam, Stefan,Rissanen, Kari
, p. 895 - 900 (2007/10/02)
Helically chiral thia- and diselena-quinquephenylophanes have been synthesized starting from suitable benzene derivatives via an 8-step synthesis path.Helical thiaquinquephenylophane 9 was obtained from bis(bromomethyl)quinquephenyl 8 in cyclisation with thioacetamide under high-dilution conditions in 10percent yield.The corresponding diselenaquinquephenylophane was obtained in 17percent yield by using KSeCN and reduction.The M- and P-enantiomers of the thiaphane were separated by HPLC using the Okamoto resin.The CD and UV spectra of the pure M- and P-enantiomers of the thiaphane were recorded.X-Ray structure analyses of the racemic crystals were performed for both compounds.Unit-cell parameters: 9, a = 10.952(1), b = 11.896(2), c = 9.804(1) Angstroem, α = 104.19(1), β = 111.71(1), γ = 80.19(1) deg, V = 1146.0(3) Angstroem3; 10, a = 10.304(2), b = 15.204(4), c = 9.128(1) Angstroem, α = 105.08(2), β = 113.72(1), γ = 93.41(2) deg, V = 1242.2(5) Angstroem3.In addition, a dimeric selena-bridged quinduephenylophane was observed, and its presence confirmed by FAB-MS and 77Se NMR spectroscopy.