NISHIYAMA et Al.
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919, 1607, 1591, 1557, 1514, 1477, 1438, 1318, 1258,
REFERENCES
[
−
1
183, 1021, 976, 804, 742, 690 cm ; MS: m/z Calcd. for
1] For recent reviews concerning the chemistry of NO in the fields of
medical science and biochemistry, see: a) In Nitric Oxide; Biology
and Pathobiology (Eds: L. Ignarro, B. Fieeman), Academic Press,
C H NO Se: 319.0112; Found: 319.0128.
1
5
13
2
2
017; b) In Nitric Oxide (Eds: J.-L. Balligand, B. Mayer), Springer,
4
.2.3
1-Nitro-1-(4-methoxyphenyl)-2-
|
New York 2000.
phenylselenoethylene (3c)
[
2] For recent reviews concerning the use of NO in the organic chem-
istry, see: J. Hartung, Chem. Rev. 2009, 109, 4500.
3] a) A. Ogawa, N. Takami, M. Sekiguchi, H. Yokoyama, H. Kuniyasu,
I. Ryu, N. Sonoda, Chem. Lett. 1991, 20, 2241; b) T. G. Back, M. V.
Krishna, J. Org. Chem. 1988, 53, 2533.
1
H-NMR (400 MHz, CDCl ) δ 7.58 (s, 1H), 7.36 (s,
3
[
2
H), 7.23-7.15 (m, 2H), 7.07 (t, J = 7.6 Hz, 1H), 6.94 (d,
1
3
J = 8.8 Hz, 2H), 6.60 (d, J = 8.4 Hz, 2H), 3.69 (s, 3H); C-
NMR (100 MHz, CDCl ) δ 160.6, 160.3, 136.0, 133.5, 130.3,
3
[4] A. Ogawa, H. Yokoyama, K. Yokoyama, T. Masawaki, N. Kambe,
N. Sonoda, J. Org. Chem. 1991, 56, 5721.
1
3
1
5
3
28.7, 128.7, 128.4, 128.2, 126.7, 113.3, 55.2; IR (neat)
075, 2932, 2837, 1603, 1556, 1508, 1477, 1438, 1316, 1252,
174, 1111, 1030, 899, 834, 805, 790, 741, 691, 658, 628,
[5] a) A. Ogawa, in Main Group Metals in Organic Synthesis, Vol.
2 (Eds: H. Yamamoto, K. Oshima), Wilet-VCH: Weinheim,
Germany 2004, 813; b) A. Ogawa, in Comprehensive Organic
Synthesis II (Ed: P Knochel), Elsevier, 4.06 2014, 392; c)
A. Nomoto, S. Hayashi, T. Fujiyama, T. Ikeda, K. Hirata, J.
Tohoma, K. Kakiuchi, W. Nakanishi, A. Ogawa, Bull. Chem.
Soc. Jpn. 2014, 87, 550; d) Y. Kobiki, S. Kawaguchi, A. Ogawa,
Tetrahedron Lett. 2013, 54, 5453; e) Y. Kobiki, S. Kawaguchi,
T. Ohe, A. Ogawa, Beil. J. Org. Chem. 2013, 117, 1141; f) T.
Tamai, A. Nomoto, K. Tsuchii, Y. Minamida, T. Mitamura, M.
Sonoda, A. Ogawa, Tetrahedron 2012, 68, 10516; g) A. Ogawa,
T. Tamai, T. Mitamura, A. Nomoto, Pure Appl. Chem. 2013, 85,
−
1
58 cm : m/z Calcd. for C H NO Se: 335.0061; Found:
1
5
13
3
35.0038.
4
.2.4
1-Nitro-1-(4-fluorophenyl)-2-
|
phenylselenoethylene (3d)
1
13
H-NMR (400 MHz, CDCl ) δ 7.67-6.60 (m, 10H); C-
3
NMR (100 MHz, CDCL ) δ 164.0, 159.3, 136.3, 136.2,
3
1
33.8, 130.6, 130.5, 130.4, 130.3, 129.0, 128.8, 127.7, 115.1,
14.8; IR (neat) 3078, 1601, 1562, 1505, 1478, 1438, 1318,
259, 1230, 1157, 1096, 1000, 899, 838, 805, 740, 690, 655,
7
85 and references therein.
1
[
6] The formation of β-phenylseleno substituted vinyl carbon radical
by the addition of carbon-carbon triple bond of acetylene appears
to be the rate-determining step. See: a) O. Ito, J. Am. Chem. Soc.
1
−1
6
27, 544 cm : m/z Calcd. for C H FNO Se: 322.9861;
14 10 2
Found: 322.9874.
1
1
983, 105, 850; b) G. A. Russell, H. Tashtoush, J. Am. Chem. Soc.
983, 105, 1398.
[
7] It is shown that nitrosothiols selectively decompose via S,N ho-
molysis upon photoexcitation or thermal activation to give the cor-
responding disulfides and nitric oxide. See: a) D. L. H. Williams,
Acc. Chem. Res. 1999, 32, 869; b) M. D. Bartberger, K. N. Houk,
S. C. Powell, L. D. Mannion, K. Y. Lo, J. S. Stamler, E. J. Toone, J.
Am. Chem. Soc. 2000, 122, 5889.
4
.2.5
Mixture of (E)- and (Z)-1-nitro-2-
|
phenylseleno-1-phenyl-1-butene (3e)
1
H-NMR (400 MHz, CDCl ) δ 7.25-6.82 (m, 10H), 3.01
3
(
q, J = 7.6 Hz, 0.4H), 2.45 (q, J = 7.6 Hz, 1.6H), 1.25 (t,
1
3
J = 7.6 Hz, 0.6H), 1.00 (t, J = 7.6 Hz, 2.4H); C-NMR
[
8] Goto and Kawashima have reported the isolation of Se-
nitrososeleno. See: K. Shimada, K. Goto, T. Kawashima, N. Takagi,
Y.-K. Choe, S. Nagase, J. Am. Chem. Soc. 2004, 126, 13238.
(
100 MHz, CDCl ) δ 154.3, 146.6, 136.8, 136.8, 136.0,
3
1
35.5, 129.6, 128.7, 128.5, 128.4, 128.2, 128.1, 128.0, 127.7,
27.7, 127.7, 127.6; IR (neat) 3054, 2967, 2933, 1568, 1522,
474, 1457, 1438, 1428, 1294, 1273, 1052, 1023, 891, 755,
1
1
SUPPORTING INFORMATION
−1
7
40. 704, 692 cm : m/z Calcd. for C H NO Se: 333.0268;
16 15 2
Found: 333.0285.
Additional supporting information may be found online in
the Supporting Information section at the end of the article.
ACKNOWLEDGMENTS
How to cite this article: Nishiyama Y, Sumida M,
Sonoda N. nitroselenation of carbon-carbon triple bond
Dedicated to 82nd birthday of Professor Naomichi Furukawa.
ORCID
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