H.-J. Wu et al. / Tetrahedron 60 (2004) 3927–3934
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4.3.13. 1-(2-Phenylethynyl)-2-(3-phenylsulfonylpro-
pynyl)benzene (28). Obtained in 67% yield as an oil
according to method B. 1H NMR (CDCl3, 200 MHz) d 8.03
(td, 2H, J¼8.0, 1.4 Hz), 7.56–7.45 (m, 6H), 7.36–7.25 (m,
6H), 4.26 (s, 2H); MS (EI): 356 (Mþ, 13), 216 (18), 215
(100), 213 (25), 149(13). HRMS (EI) calcd for C23H16O2S
356.0872, found 356.0877.
4.3.19. 2-(2-(3-Formylnaphthonyl))benzonitrile (36) and
2-phenylsulfonylmethylene-1-(2-cycnobenzylidene)-
indene (37). Compound 36 was obtained in 16% yield as an
oil and compound 37 was obtained in 10% yield as an solid
according to general method. Compound 36: 1H NMR
(CDCl3, 200 MHz) d 10.49 (s, 1H), 9.13 (dd, 1H, J¼7.6,
1.2 Hz), 8.50 (s, 1H), 8.33 (dd, 1H, J¼7.6, 1.2 Hz), 7.93 (d,
1H, J¼7.6 Hz), 7.75–7.66 (m, 2H), 7.68–7.32 (m, 4H); 13C
NMR (CDCl3, 50 MHz) d 191.0, 142.6, 142.0, 136.5, 135.0,
132.2, 132.2, 132.1, 130.6, 129.8, 129.6, 129.4, 128.6,
127.6, 127.5, 126.3, 124.6, 123.8. MS (EI): 257 (Mþ, 13),
242 (100), 77 (25). HRMS (EI) calcd for C18H11ON
257.0841, found 257.0840. Compound 37: 1H NMR
(CDCl3, 200 MHz) d 7.90–7.87 (m, 2H), 7.74 (d, 1H,
J¼7.6 Hz), 7.62–7.47 (m, 8H), 7.19 (d, 2H, J¼1.2 Hz),
7.07 (s, 1H), 6.81 (s, 1H); 13C NMR (CDCl3, 50 MHz) d
142.3, 139.7, 138.3, 137.1, 134.0, 133.7, 133.0, 132.4,
130.4, 129.1, 128.9, 128.7, 128.6, 128.5, 128.4, 127.2,
127.1, 126.0, 123.0, 121.6, 117.2, 112.4. MS (EI): 383 (Mþ,
10), 242 (100), 240 (50), 77 (25). HRMS (EI) calcd for
C24H17O2SN 383.0981, found 383.0970.
4.3.14. 2-(2-(2-(3-Phenylsulfonylpropynyl)phenyl)-
ethynyl)benzonitrile (29). Obtained in 81% yield as a
solid according to method B. 1H NMR (CDCl3, 200 MHz) d
8.04–8.01 (m, 2H), 7.69–7.60 (m, 4H), 7.59–7.31 (m, 7H),
4.37 (s, 2H); 13C NMR (CDCl3, 50 MHz) d 137.9, 133.9,
133.8, 132.7, 132.5, 132.4, 129.0, 128.9, 128.8, 128.7,
128.4, 126.8, 124.9, 124.4, 117.3, 115.0, 92.8, 89.3, 85.5,
81.7, 49.7. Anal. Calcd for C24H15O2SN: C, 75.57; H, 3.97;
N, 3.68. Found: C, 75.57; H, 3.97; N, 3.65.
4.3.15. 2-(3-Phenylthionylpropynyl)iodobenzene (31).
Obtained in 45% yield as an oil according to method A.
1H NMR (CDCl3, 200 MHz) d 7.75 (d, 1H, J¼8.2 Hz),
7.58–7.53 (m, 2H), 7.37–7.27 (m, 5H), 7.14 (dt, 1H, J¼2.0,
8.4 Hz), 3.92 (s, 2H); 13C NMR (CDCl3, 50 MHz) d 138.6,
135.1, 132.8, 130.2, 129.4, 129.3, 128.9, 127.6, 126.8,
100.6, 89.2, 85.3, 50.1. MS (EI): 349 (Mþ, 83), 123 (52),
114 (66), 241 (100). HRMS (EI) calcd for C18H18O2
349.9625, found 349.9627.
4.3.20. (Z,Z)-1-(2-Phenyl)-11-phenylsulfonylundeca-3,7-
diene-1,5,9-triyne (38). Obtained in 40% yield as an oil
according to method B. 1H NMR (CDCl3, 200 MHz) d
7.95–7.30 (m, 10H), 6.14–5.79 (m, 4H), 3.88 (s, 2H); 13C
NMR (CDCl3, 50 MHz) d 170.0, 134.6, 134.1, 133.8, 131.9,
130.9, 130.2, 129.8, 129.0, 128.8, 128.3, 128.2, 121.2,
120.4, 119.0, 118.3, 112.3, 112.1, 49.3. MS (EI): 356 (Mþ,
1), 156 (48), 139 (46), 91 (100). HRMS (EI) calcd for
C23H16O2S 356.0875, found 356.0877.
4.3.16. 2-(2-Phenylethynyl)-1-(3-phenylthiopropynyl)-
benzene (32). Obtained in 90% yield as an oil according to
method A. 1H NMR (CDCl3, 200 MHz) d 7.95 (td, 2H, J¼8.0,
1.4 Hz), 7.59–7.40 (m, 6H), 7.30–7.21 (m, 6H), 3.84 (s, 2H);
MS (EI): 324 (Mþ, 10), 215 (70), 213 (100), 149 (13).
HRMS (EI) calcd for C23H16S 324.0974, found 324.0970.
4.3.21. 2-Phenylsulfonylmethyl-1-(2-benzylidene)indene
(39). Obtained in 50% yield as an solid according to method
C. 1H NMR (CDCl3, 200 MHz) d 7.66–7.37 (m, 13H), 7.25
(s, 1H), 6.61 (d, 4H, J¼5.6 Hz), 6.52 (d, 1H, J¼5.6 Hz),
4.45 (s, 2H); 13C NMR (CDCl3, 50 MHz) d 145.6, 141.0,
136.3, 135.1, 133.3, 130.7, 129.7, 129.3, 128.9, 128.7,
128.6, 128.4, 127.8, 126.8, 125.2, 124.9, 123.6, 120.0,
119.5. MS (EI): 358 (Mþ, 18), 217 (100), 215 (74), 202 (53).
HRMS (EI) calcd for C23H18O2S 358.1028, found
358.1026.
4.3.17. 2-(2-(2-(3-Phenylthiopropynyl)phenyl)ethynyl)-
benzonitrile (33). Obtained in 65% yield as an oil according
to method A. 1H NMR (CDCl3, 200 MHz) d 7.67–7.16 (m,
13H), 3.98 (d, 2H, J¼4.0 Hz); 13C NMR (CDCl3, 50 MHz)
d 135.4, 132.7, 132.6, 132.5, 132.3, 132.2, 130.1, 128.8,
128.8, 128.2, 127.9, 127.0, 126.7, 125.7, 124.5, 117.5,
115.0, 94.4, 90.3, 88.9, 81.7, 46.2. MS (EI): 349 (Mþ, 35),
240 (100), 238 (53), 109 (81). HRMS (EI) calcd for
C24H15SN 349.0921, found 349.0921.
4.3.22. 5-Phenyl-naphthaldehyde (40). Obtained in 13%
yield as an solid according to method C. 1H NMR (CDCl3,
200 MHz) d 10.25 (s, 1H), 7.92 (d, 1H, J¼7.2 Hz), 7.86 (dd,
1H, J¼7.2, 1.2 Hz), 7.72 (d, 1H, J¼7.2 Hz), 7.76–7.20 (m,
3H), 7.49–7.40 (m, 4H), 7.31 (d, 1H, J¼7.4 Hz); 13C NMR
(CDCl3, 50 MHz) d 192.4, 136.4, 132.4, 131.4, 130.8, 130.4,
129.8, 129.7, 129.2, 129.1, 128.9, 128.8, 128.4, 125.2, 124.1.
MS (EI): 232 (Mþ, 39), 203 (72), 202 (63), 149(100).
HRMS (EI) calcd for C17H12O 232.0887, found 232.0884.
4.3.18. 3-Phenyl-2-phenylsulfonylmethylnaphthalene
(34) and 2-phenylsulfonyl methylene-1-benzylidene-
indene (35). Compound 34 was obtained in 42% yield
and compound 35 was obtained in 32% yield as an solid
1
according to general method C. Compound 34: H NMR
(CDCl3, 200 MHz) d 8.53 (s, 1H), 7.89 (dd, 2H, J¼7.2,
1.6 Hz), 7.68–7.31 (m, 13H), 4.53 (s, 2H); 13C NMR
(CDCl3, 50 MHz) d 146.4, 139.4, 134.2, 133.9, 133.5,
133.2, 132.6, 131.7, 129.9, 129.3, 129.3, 129.0, 128.9,
128.8, 128.5, 128.2, 127.8, 54.5. MS(EI): 358 (Mþ, 10), 215
(100), 149 (32). HRMS (EI) calcd for C23H18O2S 358.1028,
found 358.1023. Compound 35: 1H NMR (CDCl3,
200 MHz) d 7.83 (dd, 2H, J¼7.0, 1.6 Hz), 7.81–7.16 (m,
11H), 6.98–6.90 (m, 2H), 6.81 (s, 1H), 4.41(s, 2H); 13C
NMR (CDCl3, 50 MHz) d 142.2, 139.0, 138.4, 135.8, 135.4,
134.5, 133.7, 132.6, 129.2, 128.9, 128.9, 128.8, 128.4,
128.3, 128.1, 125.7, 121.2, 55.4. HRMS (EI) calcd for
C23H18O2S 358.1028, found 358.1027.
4.3.23. (Z)-1-Phenyl-3-hexen-1,5-diyne (42). Obtained in
68% yield as an oil according to method A. 1H NMR
(CDCl3, 200 MHz) d 7.53–7.30 (m, 5H), 5.89 (d, 2H,
J¼7.0 Hz), 3.42 (s, 1H); 13C NMR (CDCl3, 50 MHz) d
129.6, 126.5, 126.2, 121.1, 118.6, 117.3, 101.2, 100.2, 95.5,
85.0; MS (EI): 152 (Mþ, 100). HRMS (EI) calcd for C12H18
152.0626, found 152.0625.
4.3.24. (Z,Z)-1-Phenyl-11-phenylthioundeca-3,7-diene-
1,5,9-triyne (43). Obtained in 32% yield as an oil according