Full Paper
Compound 30a: Yellow liquid, 78 %. 1H NMR (400 MHz, CDCl3):
δ = 1.84 (s, 9 H), 3.34 (d, J = 16.48 Hz, 2 H), 3.79 (dd, J1 = 3.25, J2 =
16.75 Hz, 2 H), 4.48 (s, 2 H), 7.17–7.26 (m, 3 H) ppm. 13C NMR
(125 MHz, CDCl3): δ = 29.1, 33.6, 45.78, 45.84, 62.5, 65.6, 124.9,
Acknowledgments
We are grateful to Department of Science and Technology
(DST), New Delhi for the financial support (EMR/2015/002053).
G. S. thanks the Council of Scientific and Industrial Research
125.2, 128.7, 137.6, 139.6, 139.9, 179.6, 201.4 ppm. IR: νmax = 3015,
˜
2959, 2923, 2856, 1738, 1699, 1491, 1434, 1369, 1311, 1258, 1218, (CSIR)-New Delhi for the award of research fellowship. S. K.
1187, 1143, 1074, 1007 cm–1
.
thanks the Department of Science and Technology (DST) for
the award of J. C. Bose fellowship (SR/S2/JCB-33/2010) and Praj
industries for Pramod Chaudhari Chair Professor (Green chemis-
try). We also thank Mr. Darshan Mhatre for helping in collecting
the X-ray crystal data.
1
Compound 30b: Yellow solid, 70 %. H NMR (500 MHz, CDCl3): δ =
1.83 (s, 9 H), 3.34 (d, J = 16.70 Hz, 2 H), 3.78 (d, J = 16.70 Hz, 2 H),
4.64 (s, 4 H), 7.23 (s, 2 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 29.1,
30.1, 45.8, 62.2, 65.7, 127.1, 136.4, 140.8, 179.6, 201.1 ppm. IR: ν
=
˜
max
2975, 2935, 1732, 1657, 1446, 1367, 1286, 1266, 1215, 1173, 1049,
992 cm–1. HRMS (ESI, Q-ToF) m/z: calculated for [M + Na]+
C17H19Br2NNaOS2 497.9167, found 497.9168 and other isotopic
peaks are 499.9138 and 501.9139.
Keywords: [2+2+2] Cyclotrimerization · Mo(CO)6
O-Xylylene dibromide · Propargyl halides · Spirorhodanine
·
Compound 30c: Fluorescent yellow liquid, 81 %. 1H NMR (500 MHz,
CDCl3): δ = 1.84 (s, 9 H), 3.35 (d, J = 16.45 Hz, 2 H), 3.79 (dd, J1 =
5.70, J2 = 16.45 Hz, 2 H), 4.57 (s, 2 H), 7.19–7.26 (m, 3 H) ppm. 13C
NMR (125 MHz, CDCl3): δ = 29.1, 45.8, 46.3, 62.6, 65.6, 124.8, 128.3,
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137.3, 139.5, 139.9, 179.6, 201.4 ppm. IR: ν = (max3018), 2976, 2931,
˜
1737, 1492, 1435, 1400, 1368, 1286, 1265, 1175, 1117, 1085, 1049,
993 cm–1. HRMS (ESI, Q-ToF) m/z: calculated for [M + Na]+
C16H18ClNNaOS2 362.0411, found 362.0412.
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(d, J = 16.60 Hz, 2 H), 4.72 (s, 4 H), 7.26 (s, 2 H) ppm. 13C NMR
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179.5, 201.1 ppm. IR: νmax = 3018, 2976, 2933, 1732, 1449, 1426,
˜
1400, 1368, 1293, 1272, 1174, 1085, 1050, 993 cm–1. HRMS (ESI, Q-
ToF) m/z: calculated for [M + Na]+ C17H19Cl2NNaOS2 410.0177, found
410.0176.
Compound 31a: Light brown liquid, 76 %. 1H NMR (500 MHz,
CDCl3): δ = 3.40 (d, J = 16.40 Hz, 2 H), 3.46 (s, 3 H), 3.84–3.88 (dd,
J1 = 4.20, J2 = 16.40 Hz, 2 H), 4.49 (s, 2 H), 7.21 (d, J = 8.20 Hz, 1 H),
7.28 (m, 2 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 31.9, 33.5, 46.80,
46.81, 64.9, 124.9, 125.3, 128.9, 137.8, 139.5, 139.8, 178.6, 200.0 ppm.
IR: νmax = 932, 1004, 1122, 1213, 1275, 1303, 1345, 1421, 1492, 1682,
˜
1725, 2851, 2922, 3016 cm–1. HRMS (ESI, Q-ToF) m/z: calculated for
[M + Na]+ C13H12BrNNaOS2 363.9436, found 363.9436 and other
isotopic peak is 365.9421.
Compound 31b: Light brown solid, 69 %. M.p. 220–222 °C. 1H NMR
(400 MHz, CDCl3): δ = 3.41 (d, J = 16.65 Hz, 2 H), 3.46 (s, 3 H), 3.86
(d, J = 16.60 Hz, 2 H), 4.65 (s, 4 H), 7.26 (s, 2 H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 30.1, 31.9, 46.8, 64.6, 127.2, 136.5, 140.6,
178.5, 199.7 ppm. IR: νmax = 2917, 2854, 1730, 1426, 1350, 1306,
˜
1276, 1215, 1134, 1123, 1014, 932 cm–1. HRMS (ESI, Q-ToF) m/z:
calculated for [M
+
Na]+ C14H13Br2NNaOS2 455.8698, found
455.8698 and other isotopic peaks are 457.8689 and 459.8654.
Compound 32a: Brown high density liquid, 78 %. 1H NMR
(500 MHz, CDCl3): δ = 2.75 (s, 3 H), 3.33 (d, J = 16.55 Hz, 2 H), 3.80
(dd, J1 = 3.20, J2 = 16.55 Hz, 2 H), 4.49 (s, 2 H), 7.19–7.27 (m, 3 H)
ppm. 13C NMR (125MHz, CDCl3): δ = 16.4, 33.6, 47.1, 72.0, 124.7,
125.1, 128.6, 137.4, 140.6, 140.9, 190.9, 201.6 ppm. IR: νmax = 932,
˜
1004, 1122, 1213, 1275, 1303, 1345, 1421, 1492, 1682, 1725, 2851,
2922, 3016 cm–1. HRMS (ESI, Q-ToF) m/z: calculated for [M + H]+
C13H13BrNOS2 341.9616, found 341.9615 and other isotopic peak is
343.9598.
CCDC 1835689 (for 20), 1835688 (for 21), 1835686 (for 28) contain
Eur. J. Org. Chem. 0000, 0–0
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