246 Alam et al.
871, 759, 703 cm−1; EIMS (70 eV) m/z 436 (M+); Anal.
Calcd for C32H20S: C, 88.04; H, 4.62; S, 7.35. Found:
C, 87.87; H, 4.62; S, 7.53.
organic products were extracted twice with the ex-
cess chloroform, dried over anhydrous MgSO4, and
the residual solvent was removed in vacuo. The prod-
uct was isolated after dry bed column chromatogra-
phy by using n-hexane 100% as an eluent (40 mg,
29%). All spectral data are similar to those reported
in the literature [7,14].
4,4ꢀ-Diphenyldinaphtho[1,2-b:2ꢀ,1ꢀ-
d]selenophene (7)
Colorless plates; mp 256.7–257.2◦C; 1H NMR
(CDCl3) δ 7.55 (m, 2H, ArH), 7.63 (m, 2H, ArH),
7.88 (d, 2H, J = 8.7 Hz, ArH), 7.98 (d, 2H, J = 8.2
Hz, ArH), 8.20 (d, 2H, J = 8.7 Hz, ArH), 8.23 (d, 2H,
J = 8.4 Hz, ArH); EIMS (70 eV) m/z 284 (M+).
The product was also synthesized in 11% yield by
following the above procedure. Two equivalents of
elemental selenium was used in place of sulfur. Col-
1
orless needles; mp 231–231.2◦C; H NMR (CDCl3) δ
7.43–7.54 (m, 8H, ArH), 7.55–7.59 (m, 4H, ArH), 7.63
(m, 2H, ArH), 7.99 (m, 2H, ArH), 8.11 (m, 2H, ArH),
8.13 (s, 2H, ArH); 13C NMR (CDCl3) δ 121.4, 126.4,
126.5, 126.6, 126.9, 127.5, 128.3, 129.8, 130.0, 132.4,
132.9, 133.0, 140.2, 141.6; IR (KBr) 3050, 1492, 1407,
871, 759, 695 cm−1; EIMS (70 eV) m/z 484 (M+);
HR-APCI-TOFMS Calcd for C32H20Se[M]+: 484.0724.
Found: 484.0717.
Dinaphtho[1,2-b:2ꢀ,1ꢀ-d]selenophene (4)
The product was synthesized in 31% yield by the
procedure mentioned above. Two equivalents of el-
emental selenium was used in place of sulfur. Silky
1
white plates; mp 292.5–293◦C; H NMR (CDCl3) δ
7.54–7.64 (m, 4H, ArH), 7.92 (d, 2H, J = 8.5 Hz,
ArH), 7.97 (m, 2H, ArH), 8.05 (m, 2H, ArH), 8.20
(d, 2H, J = 8.5 Hz, ArH); 13C NMR (CDCl3) δ 121.1,
126.1, 126.2, 126.3, 127.0, 128.9, 131.5, 132.3, 136.9,
139.3; IR (KBr) 3049, 1511, 1378, 1309, 1251, 806,
741, 652, 527 cm−1; EIMS (70 eV) m/z 332 (M+), 252
(M+–Se); Anal. Calcd for C20H12Se: C, 72.51; H, 3.65.
Found: C, 72.29; H, 3.97.
1,1ꢀ-Bis(N,N-dimethylaminosulfonylnaphthyl)-
4,4ꢀ-bis(phenyl)-2,2ꢀ-diselenide (8)
The experimental procedure was the same as the
above procedure. Two equivalents of elemental se-
lenium was used in place of sulfur. Both products 7
and 8 were isolated in 11% and 15% yield, respec-
tively, by eluting with chloroform on silica gel col-
umn chromatography. Recrystallization from ether
afforded pure 8. Silky white solid; mp 226◦C; 1H
NMR (CDCl3) δ 2.75 (s, 12H, NMe2), 7.05 (m, 4H,
ArH), 7.19 (m, 4H, ArH), 7.30 (m, 2H, ArH), 7.44 (t,
2H, J = 7.5 Hz, ArH), 7.62 (t, 2H, J = 7.8 Hz, ArH),
7.83 (d, 2H, J = 8.4 Hz, ArH), 7.94 (s, 2H, ArH), 8.79
(d, 2H, J = 8.4 Hz, ArH); 13C NMR (CDCl3) δ 36.8,
124.8, 126.3, 127.1, 127.9, 128.1, 128.4, 129.0, 129.5,
129.9, 131.5, 131.8, 133.8, 139.0, 145.4; IR (KBr)
1323, 1151, 961, 714 cm−1; EIMS (70 eV) m/z 700
(M+−Se); Anal. Calcd for C36H32N2O4S2Se2: C, 55.53;
H, 4.14; N, 3.60. Found: C, 55.83; H, 4.04; N, 3.31.
1,1ꢀ-Bis(N,N-dimethylaminosulfonyldinaphthyl)-
2,2ꢀ-diselenide (5)
This product was isolated along with product 4.
Recrystallization from CH2Cl2 afforded pure 5 in
25% yield. Light yellow powder; mp 235◦C; 1H
NMR (CDCl3) δ 2.93 (s, 12H, NMe2), 7.52 (t, 2H,
J = 7.4 Hz, ArH), 7.63 (t, 2H, J = 7.4 Hz, ArH), 7.77
(m, 2H, ArH), 7.80 (m, 2H, ArH), 8.05 (d, 2H, J =
8.8 Hz, ArH), 8.31 (d, 2H, J = 8.8 Hz, ArH); 13C NMR
(CDCl3) δ 36.9, 124.5, 126.4, 127.6, 128.3, 128.8, 130,
131.2, 133.1, 133.9, 134.6; IR (KBr) 1332, 1315, 1148
cm−1; EIMS (70 eV) m/z 628 (M+); Anal. Calcd for
C24H24N2O4S2Se2: C, 46.01; H, 3.86; N, 4.47. Found:
C, 46.29; H, 4.17; N, 4.27.
2-Methylnaphthalene-1-sulfonic Acid
Dimethylamide (12)
Substrate 1 was dissolved in TMEDA, and n-BuLi
was added into the solution. The resulted lithiated
mixture was stirred for 6 h in ice bath at 0◦C. The ex-
cess (10 eq.) CH3I was added slowly into the reactor,
and suddenly the solution turned into a pasty mass.
Dried THF was added into the reactor, and after
30 min unreacted CH3I was removed by evapora-
tion. The resultant reaction mixture was quenched
over aqueous NaHSO3 solution. The organic product
was extracted with CHCl3, dried over MgSO4, and the
solvent was removed in vacuo. Running a silica gel
4,4ꢀ-Diphenyldinaphtho[1,2-b:2ꢀ,1ꢀ-d]thiophene(6)
The product was synthesized in 37% yield accord-
ing to the above procedure. Compound 2 was used
as the starting material. Colorless needles; mp 213–
213.5◦C; 1H NMR (CDCl3) δ 7.44–7.53 (m, 8H, ArH),
7.55–7.58 (m, 4H, ArH), 7.64 (m, 2H, ArH), 8.00
(m, 2H, ArH), 8.14 (s, 2H, ArH), 8.31 (m, 2H, ArH);
13C NMR (CDCl3) δ 120.7, 124.6, 126.2, 126.7, 127.4,
127.5, 128.3, 129.3, 130.3, 130.7, 133.4, 136.5, 138.3,
140.7; IR (KBr) 3052, 2927, 1603, 1494, 1406, 1364,
Heteroatom Chemistry DOI 10.1002/hc