1968
Helvetica Chimica Acta – Vol. 95 (2012)
Compound 13 was prepared from cyclohexane-1,4-dione via a Wittig reaction with (2-bromoben-
t
zyl)triphenylphosphonium bromide (2.1 equiv.) with BuOK (2.1 equiv.) as base, in THF at 08. Yield:
42% (cis/trans ca. 1:1). Rf (AcOEt/hexane 1:10) 0.83. IR (NaCl): 3016, 2962, 1463, 1431, 1215, 1024, 756,
669. HR-ESI-MS: 416.9872 ([M þ H]þ, C20H1979Br2þ ; calc. 416.9853).
Data of cis-13. White powder recrystallized from CH2Cl2. M.p. 978. 1H-NMR (400 MHz): 7.56 (d, J ¼
8.0, 2 H); 7.17 – 7.25 (m, 4 H); 7.07 (t, J ¼ 7.8, 2 H); 6.29 (s, 2 H); 2.51 (s, 4 H); 2.28 (s, 4 H). 13C-NMR
(100 MHz): 142.5; 138.2; 132.5; 130.9; 127.9; 126.8; 124.3; 122.937.9; 29.8.
Data of trans-13. Colorless crystals from hexanes/CH2Cl2. M.p. 1778. 1H-NMR (400 MHz): 7.59 (dd,
J ¼ 8.0, 2 H); 7.22 – 7.30 (m, 4 H); 7.10 (t, J ¼ 7.6, 2 H); 6.27 (s, 2 H); 2.37 – 2.43 (m, 8 H). 13C-NMR
(100 MHz): 142.5; 138.1; 132.4; 130.9; 127.9; 126.8; 124.3; 122.9; 37.1; 30.5.
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