584
H. Maeda et al.
(de) of 4,4-dicyano-5-methyl-6-phenyl-1-heptene (3) and 1,1-dicyano-2-methyl-3-
phenylbutane (4) were determined by GC and 1H NMR analysis (Table 1). Relative
experimental errors are within 1% (GC) and 5% (1H NMR), respectively. Separation
of syn-4 and anti-4 was performed by recycling preparative HPLC (GPC, CHCl3).
Data for the mixture of anti-3 and syn-3: 1H NMR (300 MHz, CDCl3) d 1.10–1.17
(m, 3 H), 1.40–1.49 (m, 3 H), 2.19–2.30 (m, 1 H), 2.52–2.80 (m, 2 H), 3.27–3.40 (m,
1 H), 5.33–5.46 (m, 2 H), 5.79–5.98 (m, 1 H), 7.10–7.40 (m, 5 H) ppm. Data for
anti-3: MS (EI) m/z (relative intensity, %) = 77 (73), 105 (100), 238 (6, M?);
retention time of GC = 38.6 min. Data for syn-3: MS (EI) m/z (relative intensity,
%) = 77 (79), 105 (100), 238 (9, M?); retention time of GC = 38.3 min. Data for
anti-4: 1H NMR (300 MHz, CDCl3) d 1.13 (d, J = 6.9 Hz, 3 H), 1.38
(d, J = 7.1 Hz, 3 H), 2.35 (m, J = 7.0 Hz, 1 H), 2.94 (quint, J = 7.3 Hz, 1 H),
3.72 (d, J = 5.9 Hz, 1 H), 7.16–7.37 (m, 5 H) ppm; MS (EI) m/z (relative intensity,
%) = 77 (14), 105 (100), 198 (6, M?); retention time of GC = 28.6 min. Data
for syn-4: 1H NMR (300 MHz, CDCl3) d 1.37 (d, J = 6.9 Hz, 3 H), 1.45
(d, J = 6.7 Hz, 3 H), 2.21–2.33 (m, 1 H), 2.65–2.78 (m, 1 H), 3.38 (d, J = 3.6 Hz,
1 H), 7.17–7.37 (m, 5 H) ppm; MS (EI) m/z (relative intensity, %) = 77 (21),
105 (100), 198 (5, M?); retention time of GC = 26.0 min.
Acknowledgments This work was partially supported by Grant-in-Aids for Scientific Research on
Priority Areas ‘‘Reaction Control of Dynamic Complexes (420)’’ (16033252), ‘‘Advanced Molecular
Transformations of Carbon Resources (444)’’ (18037063, 19020060), Scientific Research (B)
(15350026), and Young Scientists (B) (16750039), and the Cooperation for Innovative Technology
and Advanced Research in Evolutional Area (CITY AREA) program from the Ministry of Education,
Culture, Sports, Science and Technology (MEXT) of Japan.
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