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DONGAMANTI et al.
7,8-Dihydrodibenzo[f,k][1,5]dioxacyclododecin-
6.92–7.01 m (4H, Ar-H), 7.28–7.32 m (1H, Ar-H),
7.40–7.46 m (2H, Ar-H), 7.59–7.62 d.d (J = 7.52 Hz,
1.75 Hz, 1H, Ar-H), 7.64–7.68 d (J = 16.06 Hz, 1H),
7.78–7.82 d (J = 16.06 Hz, 1H). 13C NMR spectrum,
δC, ppm: 21.3, 21.4, 25.9, 26.7, 64.5, 68.9, 115.0,
115.7, 121.5, 122.0, 122.9, 127.8, 128.7, 129.3, 130.8,
131.8, 133.7, 139.8, 157.8, 159.3, 191.0. Found, %: C
78.20; H 6.91. C21H22O3. Calculated, %: C 78.23; H
6.88. M 323.
14(6H)-one (5a). Yield 85%. Light yellow solid; mp
96–98°C. IR spectrum, ν, cm–1: 1625, 1616, 1454,
1
1294, 1280. H NMR spectrum, δ, ppm: 2.23–2.29 m
(2H), 4.14–4.17 t (J = 5.27 Hz, 2H), 4.39–4.41 t (J =
5.52 Hz, 2H), 7.07–7.17 m (4H, Ar-H), 7.28–7.32 m
(1H, Ar-H), 7.34–7.37 d.d (J = 7.52 Hz, 1.75 Hz, 1H,
Ar-H), 7.47–7.53 m (2H, Ar-H), 7.57–7.61 d (J =
16.06 Hz, 1H), 7.70–7.73 d.d (J = 7.52 Hz, 1.75 Hz,
1H, Ar-H). 13C NMR spectrum, δС, ppm: 29.4, 66.6,
69.3, 116.0, 120.4, 122.3, 123.8, 128.9, 130.3, 130.5,
130.7, 131.5, 132.6, 133.2, 138.2, 158.1, 158.2, 193.0.
Found, %: C 77.05; H 5.82. C18H16O3. Calculated, %:
C 77.12; H 5.75. M 281.
12-Chloro-7,8-dihydrodibenzo[f,k][1,5]dioxa-
cyclododecin-14(6H)-one (5e). Yield 84%. Light
yellow solid; mp 200–202°C. IR spectrum, ν, cm–1:
1
1630, 1610, 1449, 1296, 1284. H NMR spectrum, δ,
ppm: 2.23–2.29 m (2H), 4.13–4.16 t (J = 5.27 Hz, 2H),
4.36–4.38 t (J = 5.52 Hz, 2H), 7.07–7.14 m (3H, Ar-H),
7.29–7.37 m (2H, Ar-H), 7.42–7.45 d.d (J =
8.78 Hz, 2.76 Hz, 1H, Ar-H), 7.49–7.53 d (J = 16.31
Hz, 1H), 7.56–7.60 d (J = 16.3 Hz, 1H), 7.682–7.689 d
(J = 2.76 Hz, 1H, Ar-H). 13C NMR spectrum, δC, ppm:
29.3, 67.1, 69.3, 117.5, 120.3, 123.9, 127.6, 128.6,
130.3, 130.6, 131.6, 131.7, 131.9, 132.8, 139.0, 156.6,
158.1, 191.4. Found, %: C 68.73; H 4.75. C18H15ClO3.
Calculated, %: C 68.68; H 4.80. M 315.
8,9-Dihydro-6H-dibenzo[g,l][1,6]dioxacyclo-
tridecin-15(7H)-one (5b). Yield 80%. Light yellow
solid; mp 122–124°C. IR spectrum, ν, cm–1: 1631,
1
1610, 1452, 1291, 1282. H NMR spectrum, δ, ppm:
2.16–2.17 m (4H), 4.10–4.12 m (4H), 6.87–6.89 d (J =
8.03 Hz, 1H, Ar-H), 6.91–6.93 d (J = 8.03 Hz, 1H, Ar-H),
6.95–6.99 m (1H, Ar-H), 7.01–7.05 m (1H, Ar-H),
7.26–7.31 m (1H, Ar-H), 7.40–7.43 d.d (J = 7.52 Hz,
1.50 Hz, 1H, Ar-H), 7.44–7.49 m (1H, Ar-H), 7.61–
7.65 d (J = 15.8 Hz, 1H), 8.06–8.09 d.d (J = 7.78 Hz,
2.0 Hz, 1H, Ar-H), 8.92–8.96 d (J = 15.8 Hz, 1H). 13C
NMR spectrum, δC, ppm: 25.9, 26.9, 68.3, 69.0, 111.6,
112.2, 120.6, 120.7, 124.5, 127.6, 130.4, 131.6, 132.0,
134.0, 134.3, 138.8, 159.0, 159.4, 190.5. Found, %: C
77.44; H 6.25. C19H18O3. Calculated, %: C 77.53; H
6.16. M 295.
13-Chloro-8,9-dihydro-6H-dibenzo[g,l][1,6]-
dioxacyclotridecin-15(7H)-one (5f). Yield 78%. Light
yellow solid; mp 186–188°C. IR spectrum, ν, cm–1:
1
1623, 1612, 1453, 1291, 1278. H NMR spectrum, δ,
ppm: 2.14–2.20 m (4H), 4.10–4.14 m (4H), 6.85–6.89
m (2H, Ar-H), 6.96–7.00 m (1H, Ar-H), 7.28–7.32 m
(1H, Ar-H), 7.39–7.43 m (2H, Ar-H), 7.62–7.66 d (J =
15.8 Hz, 1H), 8.03–8.05 m (1H, Ar-H), 8.90–8.94 d
(J = 15.8 Hz, 1H). 13C NMR spectrum, δC, ppm: 25.9,
26.8, 68.3, 69.5, 111.6, 113.7, 120.7, 124.2, 126.0,
128.6, 130.6, 130.9, 131.5, 133.4, 134.5, 139.6, 157.9,
159.0, 189.0. Found, %: C 69.45; H 5.17. C19H17ClO3.
Calculated, %: C 69.41; H 5.21. M 329.
7,8,9,10-Tetrahydrodibenzo[h,m][1,7]dioxacyclo-
tetradecin-16(6H)-one (5c). Yield 75%. Light yellow
solid; mp 112–115°C. IR spectrum, ν, cm–1: 1653,
1
1604, 1450, 1332, 1284. H NMR spectrum, δ, ppm:
1.87–2.01 m (6H), 4.13–4.15 t (J = 4.76 Hz, 2H), 4.20–
4.23 t (J = 5.52 Hz, 2H), 6.88–6.90 d (J = 8.28 Hz, 1H,
Ar-H), 6.95–7.02 m (3H, Ar-H), 7.28–7.32 m (1H, Ar-H),
7.40–7.42 m (2H, Ar-H), 7.67–7.73 m (2H, Ar-H),
8.19–8.23 d (J = 15.8 Hz, 1H). 13C NMR spectrum, δC,
ppm: 21.1, 25.9, 26.6, 64.6, 68.2, 111.6, 112.2, 120.6,
120.7, 124.1, 129.7, 130.2, 130.8, 131.0, 132.9, 134.8,
139.6, 157.6, 159.4, 193.5. Found, %: C 77.96; H 6.60.
C20H20O3. Calculated, %: C 77.90; H 6.54. M 309.
14-Chloro-7,8,9,10-tetrahydrodibenzo[h,m][1,7]-
dioxacyclotetradecin-16(6H)-one (5g). Yield 75%.
Light yellow solid; mp 132–134°C. IR spectrum, ν, cm–1:
1
1629, 1611, 1457, 1293, 1281. H NMR spectrum, δ,
ppm: 1.89–1.97 m (6H), 4.13–4.16 m (2H), 4.18–4.21
m (2H), 6.88–6.90 d (J = 8.28 Hz, 1H, Ar-H), 6.93–
6.99 m (2H, Ar-H), 7.29–7.33 m (1H, Ar-H), 7.36–
7.39 d.d (J = 8.78 Hz, 2.76 Hz, 1H, Ar-H), 7.40–7.42
d.d (J = 7.52 Hz, 1.50 Hz, 1H, Ar-H), 7.651–7.652 d
(J = 2.76 Hz, 1H, Ar-H), 7.68–7.72 d (J = 15.8 Hz,
1H), 8.13–8.17 d (J = 15.81 Hz, 1H). 13C NMR spec-
trum, δC, ppm: 21.0, 25.9, 26.5, 65.1, 68.2, 112.2,
113.1, 120.8, 123.9, 125.8, 129.0, 130.7, 131.1, 131.2,
8,9,10,11-Tetrahydro-6H-dibenzo[i,n][1,8]dioxa-
cyclopentadecin-17(7H)-one (5d). Yield 68%. Light
yellow solid; mp 102–104°C. IR spectrum, ν, cm–1:
1
1635, 1611, 1448, 1304, 1285. H NMR spectrum, δ,
ppm: 1.63–1.71 m (4H), 1.81–1.85 m (4H), 4.15–4.18
t (J = 5.52 Hz, 2H), 4.26–4.28 t (J = 5.27 Hz, 2H),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 7 2016