Page 21 of 37
The Journal of Organic Chemistry
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(
4aR,8aR,1’E,1’’E)-2,6-Di(3-chloroprop-1-en-1-yl)-4,4,8,8-tetrakis(4-fluoro-
phenyl)tetrahydro[1,3,2]dioxaborinino[5,4-d][1,3,2]dioxaborinin [(R,R)-5b]
Yield: 97%, 2.0 g (3.0 mmol); white solid. R (n-pentane:Et O 90:10): 0.36. Mp: 99.7–
f
2
02.3 °C. [α]D20 +38 (c 1.0, CHCl ). H NMR (600 MHz, CDCl ): δ 4.11 (dd, J = 1.5 Hz,
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3 3
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.9 Hz, 4 H), 4.71 (s, 2 H), 5.78 (d, J = 17.5 Hz, 2 H), 6.63 (dt, J = 5.9 Hz, 17.5 Hz,
2 H), 6.98 (t, J = 8.7 Hz, 4 H), 7.08 (t, J = 8.5 Hz, 4 H), 7.19–7.24 (m, 4 H), 7.34–7.40
m, 4 H) ppm. 13C{ H} NMR (151 MHz, CDCl ): δ 46.1, 69.0, 80.4, 115.1 (d, J =
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(
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1.5 Hz), 116.3 (d, J = 21.5 Hz), 125.0, 126.7 (d, J = 8.1 Hz), 128.1 (d, J = 7.9 Hz),
137.6 (d, J = 3.2 Hz), 139.0 (d, J = 3.3 Hz), 146.3, 162.1 (d, J = 246.7 Hz), 162.4 (d, J
=
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248.6 Hz) ppm. IR (ATR): 휈 1713, 1640, 1603, 1506, 1363, 1328, 1266, 1219, 1160,
–1
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92, 832, 739, 702, 585, 567 cm . The analytics are in alignment with the literature.
(
4aR,8aR,1’E,1’’E)-2,6-Di(3-chloroprop-1-en-1-yl)-4,4,8,8-tetrakis[4-(trifluorome-
thyl)phenyl]tetrahydro[1,3,2]dioxaborinino[5,4-d][1,3,2]dioxaborinin [(R,R)-5c]
Yield: 93%, 2.2 g (2.5 mmol); white solid. R (n-pentane:Et O 90:10): 0.26. Mp: 108.1–
f
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09.5 °C. [α]D20 +48 (c 1.1, CHCl ). H NMR (600 MHz, CDCl ): δ 4.12 (dd, J = 1.4 Hz,
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.9 Hz, 4 H), 4.87 (s, 2 H), 5.79 (dd, J = 1.5 Hz, 17.5 Hz, 2 H), 6.64 (dt, J = 5.8 Hz,
17.5 Hz, 2 H), 7.43 (d, J = 8.2 Hz, 4 H), 7.53–7.60 (m, 8 H), 7.70 (d, J = 8.3 Hz, 4 H)
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ppm. C{ H} NMR (151 MHz, CDCl ): δ 45.8, 68.7, 80.4, 124.1, 125.2, 125.3 (d, J =
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.6 Hz), 126.4, 126.5 (d, J = 3.6 Hz), 127.7, 130.0 (q, J = 32.6 Hz), 131.0 (q, J =
33.0 Hz), 145.4 (d, J = 206.1 Hz), 146.8 ppm. IR (ATR): 휈 1641, 1616, 1461, 1321,
–1
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220, 1209, 1166, 1122, 1069, 1017, 992, 908, 851, 821, 773, 733, 649, 597 cm .
+
HRMS: m/z [M + NH ] calcd. 884.1541 for C H B Cl F NO ; found 884.1537.
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(4aR,8aR,1’E,1’’E)-2,6-Di(3-chloroprop-1-en-1-yl)-4,4,8,8-tetrakis(3,5-difluoro-
phenyl)tetrahydro[1,3,2]dioxaborinino[5,4-d][1,3,2]dioxaborinin [(R,R)-5d]
20
Yield: 43%, 0.33 g (0.45 mmol); white solid. R (n-pentane:Et O 90:10): 0.29. [α] +15
f
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D
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(c 1.0, CHCl ). H NMR (600 MHz, CDCl ): δ 4.13 (dd, J = 1.5 Hz, 5.8 Hz, 4 H), 4.69
3 3
(s, 2 H), 5.77 (dd, J = 1.5 Hz, 17.5 Hz, 2 H), 6.63 (dt, J = 5.8 Hz, 17.5 Hz, 2 H), 6.73
(tt, J = 2.4 Hz, 8.6 Hz, 2 H), 6.82 (dd, J = 2.2 Hz, 8.1 Hz 4 H), 6.87 (tt, J = 2.3 Hz,
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.4 Hz, 2 H), 6.95 (dd, J = 2.2 Hz, 8.3 Hz, 4 H) ppm. C{ H} NMR (151 MHz, CDCl ):
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δ 45.8, 68.6, 79.8, 103.49 (t, J = 25.2 Hz), 104.7 (t, J = 25.1 Hz), 108.1 (dd, J = 5.2 Hz,
27.6 Hz), 109.1 (dd, J = 5.8 Hz, 27.0 Hz), 144.4 (t, J = 8.9 Hz), 145.8 (t, J = 7.6 Hz),
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47.3, 162.9 (dd, J = 12.8 Hz, 248.8 Hz), 163.6 (dd, J = 12.6 Hz, 252.2 Hz) ppm. IR
(ATR): 휈 1641, 1611, 1588, 1487, 1446, 1381, 1358, 1327, 1266, 1251, 1221, 1173,
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