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1-Azido-3-methoxy-1-phenylpropane (2n): Colorless oil; IR (ATR):
n˜ =2925, 2876, 2092, 1454, 1386, 1311, 1243, 1179, 1118, 1071,
(m, 1H), 2.52–2.45 (m, 1H), 2.41–2.33 (m, 1H), 1.34 ppm (d, J=
6.8 Hz, 3H).
1,3,3-Triphenyl-1-propyne (4a): The 1H NMR spectrum of the
product was identical to that given in reference [16]. 1H NMR
(500 MHz, CDCl3): d=7.49–7.44 (m, 6H), 7.34–7.30 (m, 9H),
5.21 ppm (s, 1H).
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1012 cmÀ1; H NMR (500 MHz, CDCl3): d=7.40–7.37 (m, 2H), 7.34–
7.32 (m, 3H), 4.67 (dd, J=8.5, 6.0 Hz, 1H), 3.52–3.47 (m, 1H), 3.35–
3.31 (m, 1H), 3.34 (s, 3H), 2.08–2.04 (m, 1H), 2.03–1.94 ppm (m,
1H); 13C NMR (125 MHz, CDCl3): d=139.5, 128.8, 128.2, 126.9, 68.8,
62.9, 58.7, 36.4 ppm; ESI-HRMS: m/z calcd for C10H13N3O [M]+:
191.1053; found: 191.1097.
(E)-(3-Methylpent-1-en-4-yne-1,5-diyl)dibenzene
(4b):
The
1H NMR spectrum of the product was identical to that given in ref-
erence [17]. 1H NMR (400 MHz, CDCl3): d=7.45 (d, J=7.2 Hz, 2H),
7.39 (d, J=7.6 Hz, 2H), 7.34–7.29 (m, 5H), 7.23 (d, J=8.8 Hz, 1H),
6.68 (d, J=7.6 Hz, 1H), 6.24 (dd, J=7.6, 6.0 Hz, 1H), 3.57–3.53 (m,
1H), 1.45 ppm (d, J=6.0, 3H).
1-Azido-3-benzyloxy-1-phenylpropane(2s): Colorless oil; IR (ATR):
n˜ =3031, 2859, 2092, 1494, 1453, 1362, 1244, 1101, 1070,
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1027 cmÀ1; H NMR (500 MHz, CDCl3): d=7.38–7.29 (m, 10H), 4.71
(dd, J=8.0, 7.0 Hz, 1H), 4.51 (d, J=12.0 Hz, 1H), 4.47 (d, J=
12.0 Hz, 1H), 3.61–3.57 (m, 1H), 3.44–3.40 (m, 1H), 2.12–2.06 (m,
1H), 2.03–1.96 ppm (m, 1H); 13C NMR (100 MHz, CDCl3): d=140.2,
138.2, 138.1, 128.4, 128.1, 127.8, 127.7, 126.4, 72.2, 71.7, 60.8,
21.6 ppm; ESI-HRMS: m/z calcd for C16H17N3ONa [M+Na]+:
290.1264; found: 290.1256.
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2,2-Diphenylacetonitrile (5a): The H NMR spectrum of the prod-
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uct was identical to that given in reference [18]. H NMR (400 MHz,
CDCl3): d=7.39–7.30 (m, 10H), 5.13 ppm (s, 1H).
(E)-2-Methyl-4-phenyl-3-butenenitrile (5ba): The 1H NMR spec-
trum of the product was identical to that given in reference [19].
1H NMR (400 MHz, CDCl3): d=7.40–7.26 (m, 5H), 6.73 (d, J=
16.0 Hz, 1H), 6.07 (dd, J=16.0, 6.0 Hz, 1H), 3.55–3.47 (m, 1H),
1.52 ppm (d, J=7.2 Hz, 3H).
1-Azido-1-(4-(benzyloxymethyl)phenyl)ethane (2t): Colorless oil;
IR (ATR): n˜ =2927, 2855, 2090, 1496, 1453, 1421, 1376, 1359, 1304,
;
1242, 1088, 1071, 1019 cmÀ1 1H NMR (500 MHz, CDCl3): d=7.40–
7.29 (m, 9H), 4.62 (q, J=7.0 Hz, 1H), 4.57 (s, 2H), 4.56 (s, 2H),
1.52 ppm (d, J=7.0 Hz, 3H); 13C NMR (125 MHz, CDCl3): d=139.5,
138.2, 128.8, 128.4, 128.2, 127.7, 127.6, 126.9, 73.1, 66.5, 63.1,
36.5 ppm; ESI-HRMS: m/z calcd for C16H17N3ONa [M+Na]+:
290.1264; found: 290.1264.
2-(1-Azidoethyl)naphthalene (2u): The 1H NMR spectrum of the
product was identical to that given in reference [8]. 1H NMR
(500 MHz, CDCl3): d=7.88–7.84 (m, 3H), 7.83 (s, 1H), 7.77–7.48 (m,
2H), 7.45 (dd, J=7.0, 1.5 Hz, 1H), 4.79 (q, J=7.0 Hz, 1H), 1.61 ppm
(d, J=7.0 Hz, 3H).
(E)-4-Methyl-2-phenyl-3-butenenitrile (5bb): Yellow oil; IR (ATR):
n˜ =3031, 2919, 2241, 1600, 1493, 1452, 1379, 1075, 1029 cmÀ1
;
1H NMR (400 MHz, CDCl3): d=7.41–7.37 (m, 2H), 7.34–7.31 (m, 3H),
5.96–5.88 (m, 1H), 5.53 (dd, J=15.2, 6.4 Hz, 1H), 4.48 (d, J=6.4 Hz,
1H), 1.76 ppm (d, J=6.4 Hz, 3H); 13C NMR (100 MHz, CDCl3): d=
135.0, 129.8, 129.1, 128.1, 127.4, 125.2, 119.2, 39.8, 17.6 ppm; ESI-
HRMS: m/z calcd for C16H17N3ONa [M+Na]+: 180.0784; found:
180.0782
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4,4-Diphenylbut-1-ene (3a): The H NMR spectrum of the product
Acknowledgements
was identical to that given in reference [15]. 1H NMR (500 MHz,
CDCl3): d=7.30–7.24 (m, 8H), 7.20–7.17 (m, 2H), 5.77–5.69 (m, 1H),
5.04 (d, J=16.5 Hz, 1H), 4.96 (d, J=10.0 Hz, 1H), 4.02 (t, J=7.0 Hz,
1H), 2.83 ppm (t, J=7.0 Hz, 2H).
This work was partially supported by a Grant-in-Aid for Young
Scientists (B) from the Japan Society for the Promotion of
Science (JSPS).
3-Methyl-1-phenylhexa-1,5-diene and 4-phenylhepta-1,5-diene
(3ba and 3bb): An approximately 2:1 mixture of inseparable 3ba
and 3bb was obtained. Colorless oil; IR (ATR): n˜ =3077, 3026, 2960,
Keywords: azides
·
chemoselectivity
·
ethers
·
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2924, 1640, 1600, 1493, 1450, 1376, 1102, 1072, 1029 cmÀ1; H NMR
functionalization · iron
(400 MHz, CDCl3): d=7.42–7.23 (m, 5H), 6.41 (d, J=16.0 Hz, 0.67H),
6.21 (dd, J=16.0, 7.6 Hz, 0.67H), 5.92–5.82 (m, 0.67H), 5.80–5.72
(m, 0.33H), 5.68–5.62 (m, 0.33H), 5.54–5.47 (m, 0.33H), 5.12–4.99
(m, 2H), 3.35 (q, J=7.2 Hz, 0.33H), 2.52–2.42 (m, 1.33H), 2.30–2.14
(m, 1.34H), 1.72 (d, J=6.4 Hz, 1H), 1.15 ppm (d, J=6.8 Hz,
2H);13C NMR (100 MHz, CDCl3): d=144.7, 137.8, 137.0, 136.0, 134.4,
128.4, 128.3, 128.2, 127.6, 126.8, 126.0, 125.9, 116.0, 115.8, 48.8,
41.4, 40.4, 36.9, 19.9, 17.9 ppm; ESI-HRMS: m/z calcd for
C16H17N3ONa [M+Na]+: 195.1144; found: 195.1139.
[1] P. G. M. Wuts, T. W. Greene, Greene’s Protective Groups in Organic Synthe-
sis, 4th ed., Wiley, Hoboken, 2007.
[5] B.-Q. Wang, S.-K. Xiang, Z.-P. Sun, B.-T. Guan, P. Hu, K.-Q. Zhao, Z.-J. Shi,
4-(4-(Benzyloxymethyl)phenyl)pent-1-ene (3d): Colorless oil; IR
(ATR): n˜ =3028, 2960, 2924, 2855, 1639, 1513, 1495, 1453, 1419,
Sawama, K. Kawamoto, H. Satake, N. Krause, Y. Kita, Synlett 2010, 14,
2151–2155; c) Y. Sawama, Y. Shishido, T. Yanase, K. Kawamoto, R. Goto,
to, H. Satake, K. Shibata, Y. Monguchi, H. Sajiki, Y. Kita, Adv. Synth. Catal.
2013, 355, 517–528.
1
1359, 1260, 1209, 1091, 1073, 1027 cmÀ1; H NMR (400 MHz, CDCl3):
d=7.39–7.29 (m, 7H), 7.18 (d, J=7.6 Hz, 2H), 5.74–5.67 (m, 1H),
5.02–4.93 (m, 2H), 4.56 (s, 2H), 4.53 (s, 2H), 2.79 (q, J=6.8 Hz, 1H),
2.40–2.34 (m, 1H), 2.31–2.26 (m, 1H), 1.24 ppm (d, J=6.8 Hz,
3H);13C NMR (100 MHz, CDCl3): d=147.3, 146.5, 138.4, 137.1, 128.4,
127.9, 127.8, 127.6, 127.0, 115.9, 72.1, 72.0, 42.6, 39.5, 21.5 ppm;
ESI-HRMS: m/z calcd for C16H17N3ONa [M+Na]+: 289.1563; found:
289.1560.
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4-Naphthylpent-1-ene (3e): The H NMR spectrum of the product
was identical to that given in reference [2a]. 1H NMR (400 MHz,
CDCl3): d=7.80–7.77 (m, 3H), 7.61 (s, 1H), 7.46–7.39 (m, 2H), 7.35
(d, J=8.4 Hz, 1H), 5.79–5.68 (m, 1H), 5.03–4.94 (m, 2H), 2.98–2.93
Chem. Eur. J. 2014, 20, 2631 – 2636
2635
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