Report of an isolated or observed compound
Name: Noriyuki SUZUKI
Title of the compound
1,1,6,6-tetrakis(4-ethylphenyl)hexapenta-1,2,3,4,5-ene
Et
Et
Et
Et
Exp. ns1045,1057 (X-ray: ns119b)
Isol. or Obs.:
Isol. Appearance; yellow needle crystals
Yield:
82% isol.
b.p or m.p. 125-127 °C 分解の場合は(dec.)と添える
H NMR (CDCl3, Me4Si):  1.27 (t, 7.6 Hz, 12H), 2.68 (q, 7.6 Hz, 8H), 7.21 (d, 8.2 Hz,
8H), 7.49 (d, 8.2 Hz, 8H).
13
C NMR (CDCl3, Me4Si):  15.46, 28.75, 123.79 (q), 126.04 (q), 128.03 (CH), 129.34
(CH), 135.76 (q, Ar), 144.87 (q, Ar), 147.84 (q). (mesd. 070412)
1
IR (nujol, cm-1): 830, 913, 1181, 1457, 1505, 1602, 1656, 1794, 1910, 1999, 2865, 2927,
2964.
Elemental Analysis calcd for C38H36 C, 92.64; H, 7.36 found C 92.53, H 7.48
High resolution MS: calcd for C38H36 = 492.28170, found = 492.xxxxx
Experimental
To a solution of diol (1.37g, 2.38 mmol) in THF (15 mL) was added anhydrous SnCl2
(1.35 g, 7.14 mmol) and hydrogen chloride in diethyl ether (2.0 M, 4.8 mL, 9.5 mmol)
at 0 °C. The solution turned dark red was stirred for 1 h at 0 °C, and 1N HCl was
added and extracted with Et2O. The organic layer was combined and dried with
MgSO4 and evaporated. Red residue was purified with column chromatograph on
silica gel (hexane/ethyl acetate = 95/5) to give the title compound as red crystals (0.965
g, 82%).
Ref.) Kuwatani, Y., Yamamoto, G., Oda, M., Masahiko Iyoda, M. Bull. Chem. Soc. Jpn.
2005, 78, 2188–2208.