10.1002/ejoc.201901689
European Journal of Organic Chemistry
MHz, CDCl3) δ 7.49 (d, 2H, J = 7.2 Hz), 7.40 (d, 2H,
J = 7.2 Hz), 7.35–7.30 (m, 4H), 7.28–7.21 (m, 2H),
6.52 (dd, 2H, J = 39.6, 16.2 Hz), 1.79 (s, 3H), 1.25 (s,
9H) ppm. 13C NMR (CDCl3, 151 MHz) δ 144.30,
137.16, 134.03, 129.96, 128.67, 128.09, 127.68,
127.25, 126.69, 126.53, 83.76, 79.42, 26.88, 24.70
1H, J = 3.2 Hz), 2.452.38 (m, 1H), 1.76–1.68 (m, 4H),
1.541.51 (m, 3H), 1.44–1.31 (m, 5H), 1.28 (s, 9H),
1.26 (s, 2H) ppm. 13C NMR (CDCl3, 101 MHz) δ
205.67, 151.54, 138.17, 134.84, 129.81, 127.85,
123.26, 82.48, 80.58, 59.97, 37.84, 32.49, 30.06, 26.72,
26.64, 26.59, 26.21, 26.02 ppm. IR (KBr): ν̃ = 2921,
ppm. IR (KBr): ν
̃
= 2988, 2935, 1891, 1736, 1677,
1718, 1602, 1464, 1362, 1195, 1021, 754 cm-1. HRMS
(ESI/Q-TOF) m/z: [M + H]+ Calcd for C21H31O3
331.2268; Found 331.2273.
1578, 1486, 1394, 1263, 1072, 1026, 1007, 927, 913,
861, 807, 757, 735, 731, 718, 667, 645 cm-1. HRMS
(ESI/Q-TOF) m/z: [M + K]+ Calcd for C20H24KO2
335.1408; Found 335.1416.
1,2-bis(tert-Butylperoxy)-2,3-dihydro-1H-indene
1
(26ae'): Yellow gummy, (88 mg, 59 %). H NMR
E-4,4'-(3-(tert-Butylperoxy)but-1-ene-1,3-
(CDCl3, 400 MHz) δ 7.48 (d, 1H, J = 7.6 Hz), 7.29 (d,
1H, J = 6.0 Hz), 7.22 (t, 2H, J = 6.0 Hz), 5.52 (d, 1H,
J = 1.6 Hz), 4.99–4.96 (m, 1H), 3.36 (dd, 1H, J = 17.2,
6.8 Hz), 2.95 (dd, 1H, J = 17.2, 2.4 Hz), 1.28 (s, 9H),
1.26 (s, 9H) ppm. 13C NMR (CDCl3, 101 MHz) δ
142.81, 138.27, 129.49, 126.92, 126.87, 125.20, 89.61,
diyl)bis(bromobenzene) (23a): Yellow gummy, (161
1
mg, 71 %). H NMR (CDCl3, 400 MHz) δ 7.647.42
(m, 4H), 7.34 (d, 2H, J = 6.0 Hz), 7.25 (d, 2H, J =
5.6Hz), 6.43 (dd, 2H, J = 36.0, 11.2 Hz), 1.75 (s, 3H),
1.23 (s, 9H) ppm. 13C NMR (CDCl3, 101 MHz) δ
143.09, 135.78, 133.99, 131.80, 131.20, 129.29,
128.43, 128.22, 121.64, 121.34, 83.39, 79.65, 26.82,
86.61, 80.68, 80.56, 35.85, 26.59 ppm. IR (KBr): ν̃ =
2976, 1717, 1466, 1341, 1195, 1020, 874, 751 cm-1.
HRMS (ESI/Q-TOF) m/z: [M + NH4]+ Calcd for
C17H30NO4 312.2169; Found 312.2143.
24.63 ppm. IR (KBr): ν̃ = 2978, 2930, 1900, 1726,
1687, 1588, 1486, 1394, 1263, 1072, 1026, 1009, 930,
909, 858, 803, 755, 745, 739, 718, 681, 668, 644 cm-1.
HRMS (ESI/Q-TOF) m/z: [M + NH4]+ Calcd for
C20H26Br2O2 470.0325; Found 470.0337.
2-(tert-Butylperoxy)-2,3-dihydro-1H-inden-1-one
1
(26af′): Brownish gummy, (67 mg, 61 %). H NMR
(CDCl3, 400 MHz) δ 7.75 (d, 1H, J = 7.6 Hz), 7.59 (t,
1H, J = 7.6 Hz), 7.38 (dd, 2H, J = 16.0, 8.0 Hz), 4.38
(dd, 1H, J = 7.6, 4.8 Hz), 3.48 (dd, 1H, J = 16.8, 8.0
Hz), 2.99 (dd, 1H, J = 16.4, 4.8 Hz), 1.34 (s, 9H) ppm.
13C NMR (CDCl3, 101 MHz) δ 205.08, 150.80, 135.41,
134.92, 127.85, 126.63, 124.30, 75.33, 74.26, 36.77,
3-(tert-Butylperoxy)-2-cyclohexyl-2,3-dihydro-1H-
inden-1-one (26ab): Yellow gummy, (98 mg, 65 %).
1H NMR (CDCl3, 400 MHz) δ 7.81 (d, 1H, J = 8.0 Hz),
7.73 (d, 1H, J = 7.6 Hz), 7.64 (t, 1H, J = 7.6, 1.1 Hz),
7.49 (t, 1H, J = 7.4 Hz), 5.45 (d, 1H, J = 2.4 Hz), 2.66
(dd, 1H, J = 4.4, 2.8 Hz), 2.11–2.04 (m, 1H), 1.79–1.74
(m, 2H), 1.66 (d, 2H, J = 7.6 Hz), 1.41 (d, 1H, J = 11.2
Hz), 1.35–1.30 (m, 2H), 1.27 (s, 9H), 1.22 (d, 1H, J =
3.6 Hz), 1.15–1.10 (m, 2H) ppm. 13C NMR (CDCl3,
101 MHz) δ 205.88, 151.09, 138.00, 134.87, 129.91,
127.84, 123.23, 82.21, 80.56, 58.32, 38.94, 31.32,
28.49 ppm. IR (KBr): ν̃ = 2971, 2925, 1723, 1664,
1606, 1366, 1265, 1193, 951, 752 cm-1. HRMS
(ESI/Q-TOF) m/z: [M + H]+ Calcd for C13H17O3
221.1172; Found 221.1199.
3-(tert-Butylperoxy)-2-(1,4-dioxan-2-yl)-2,3-
29.23, 26.75, 26.69, 26.47, 26.35 ppm. IR (KBr): ν
̃
=
dihydro-1H-inden-1-one (26ag): Brownish gummy,
1
2977, 1717, 1601, 1449, 1362, 1194, 751 cm-1. HRMS
(ESI/Q-TOF) m/z: [M + H]+ Calcd for C19H27O3
303.1955; Found 303.1981.
(86 mg, 56 %). H NMR (CDCl3, 400 MHz) δ 7.81–
7.75 (m, 2H), 7.67 (t, 1H, J = 7.4 Hz), 7.50 (t, 1H, J =
7.6 Hz), 5.80 (d, 1H, J = 2.4 Hz), 3.90–3.84 (m, 2H),
3.73–3.59 (m, 5H), 2.73 (t, 1H, J = 2.6 Hz), 1.29 (s,
9H) ppm. 13C NMR (CDCl3, 101 MHz) δ 202.76,
150.94, 137.38, 135.21, 129.92, 127.42, 123.60, 80.79,
80.30, 74.20, 69.77, 67.27, 66.54, 54.61, 26.69 ppm.
3-(tert-Butylperoxy)-2-cycloheptyl-2,3-dihydro-
1H-inden-1-one (26ac): Gummy, (100 mg, 63 %). 1H
NMR (CDCl3, 400 MHz) δ 7.84 (d, 1H, J = 8.0 Hz),
7.74 (d, 1H, J = 7.6 Hz), 7.64 (t, 1H, J = 8.0 Hz), 7.49
(t, 1H, J = 7.6 Hz), 5.45 (d, 1H, J = 2.4 Hz), 2.69 (t,
IR (KBr): ν
̃ = 2975, 2858, 1722, 1604, 1461, 1362,
1286, 1195, 1119, 876, 756, 616 cm-1. HRMS (ESI/Q-
1H, J = 3.2 Hz), 2.33–2.27 (m, 1H), 1.80–1.71 (m, 2H), TOF) m/z: [M + H]+ Calcd for C17H23O5 307.1540;
1.53–1.47 (m, 3H), 1.41–1.29 (m, 5H), 1.28 (s, 9H),
1.27 (d, 2H, J = 2.8 Hz) ppm. 13C NMR (CDCl3, 101
MHz) δ 205.67, 151.43, 138.06, 134.87, 129.84,
127.86, 123.28, 82.36, 80.58, 59.37, 40.34, 33.31,
30.82, 28.00, 27.76, 27.49, 27.33, 26.70 ppm. IR
Found 307.1555.
3-(tert-Butylperoxy)-1-phenyl-3-(p-tolyl)propan-1-
1
one (2aC): Gummy, (102 mg, 65 %). H NMR (400
MHz, CDCl3) δ 7.95 (d, 2H, J = 7.2 Hz), 7.56 (t, 1H, J
= 7.4 Hz), 7.44 (t, 2H, J = 7.6 Hz), 7.32 (d, 2H, J = 8.0
Hz), 7.16 (d, 2H, J = 8.0 Hz), 5.56 (t, 1H, J = 6.6 Hz),
3.79 (dd, 1H, J = 16.4, 7.2 Hz), 3.21 (dd, 1H, J = 16.0,
6.0 Hz), 2.33 (s, 3H), 1.16 (s, 9H) ppm. 13C NMR (101
MHz, CDCl3) δ 197.77, 138.02, 137.32, 136.95,
133.16, 129.24, 128.75, 128.63, 128.37, 127.26, 82.40,
(KBr): ν̃ = 2924, 2858, 1602, 1460, 1362, 1254, 1021,
754 cm-1. HRMS (ESI/Q-TOF) m/z: [M + H]+ Calcd
for C20H29O3 317.2111; Found 317.2129.
3-(tert-Butylperoxy)-2-cyclooctyl-2,3-dihydro-1H-
inden-1-one (26ad): Red gummy, (107 mg, 65 %). 1H
NMR (CDCl3, 400 MHz) δ 7.84 (d, 1H, J = 7.6 Hz),
7.74 (d, 1H, J = 7.6 Hz), 7.64 (t, 1H, J = 7.0 Hz), 7.48
(t, 1H, J = 7.4 Hz), 5.43 (d, 1H, J = 2.8 Hz), 2.68 (t,
80.86, 44.05, 26.47, 26.38, 21.32 ppm. IR (KBr) ν
̃ =
2979, 2933, 1608, 1518, 1372, 1261, 1199, 1014, 815,
11
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