BAUCH ET AL.
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δ = 15.6 (q; Me), 78.2 (s; C‐1, C‐4), 119.8 (d; C‐5, C‐8),
2.3.6 | 1,4‐Dibenzoyloxy‐1,4‐dihydro‐1,4‐
126.4 (d; C‐6, C‐7), 138.5 (d; C‐2, C‐3), 140.3 ppm (s;
epidioxidonaphthalene (2j)
C‐4a, C‐8a).
Photooxygenation of naphthalene 1j (55 mg, 0.15 mmol)
gave even after 600 minutes no conversion.
2
.3.2 | 1,4‐Dimethoxy‐1,4‐dihydro‐1,4‐
epidioxidonaphthalene (2e)
2.3.7 | 1,4‐Bis(trimethylsiloxy)‐1,4‐dihydro‐
1
,4‐epidioxidonaphthalene (2k)
Reaction of naphthalene 1e (28 mg, 0.15 mmol) for
3
0 minutes afforded the title compound with a conversion
Reaction of naphthalene 1k (46 mg, 0.15 mmol) for
120 minutes afforded 1,4‐naphthoquinone (4), as detected
in the crude NMR.
of 95%.
1
H NMR (500 MHz, CD Cl ): δ = 3.75 (s, 6H; OMe),
2
2
7
7
.10 (s, 2H; 2‐H, 3‐H), 7.25 to 7.29 (m, 2H; 6‐H, 7‐H),
13
.36 to 7.39 ppm (m, 2H; 5‐H, 8‐H); C NMR (100 MHz,
2
.3.8 | 1,4‐Bis(triisopropylsiloxy)‐1,4‐dihydro‐
,4‐epidioxidonaphthaline (2l)
CD Cl ): δ = 53.7 (q; OMe), 102.2 (s; C‐1, C‐4), 119.0 (d;
2
2
1
C‐5, C‐8), 126.9 (d; C‐6, C‐7), 133.5 (d; C‐2, C‐3),
37.3 ppm (s; C‐4a, C‐8a).
1
Reaction of naphthalene (1l, 71 mg, 0.15 mmol) for
20 minutes afforded the title compound with a conversion
of 99%.
1
1
H NMR (500 MHz, CD Cl ): δ = 1.04 (d, J = 7.2 Hz,
2
.3.3 | 1,4‐Diethoxy‐1,4‐dihydro‐1,4‐
2
2
1
8H; Me), 1.05 (d, J = 7.2 Hz, 18H; Me), 1.18 (sept,
epidioxidonaphthalene (2g)
J = 7.2 Hz, 6H; Si‐CH), 6.66 (s, 2H; 2‐H, 3‐H), 7.25 to
Reaction of naphthalene 1g (32 mg, 0.15 mmol) for
3
of 95%.
7
8
1
1
.28 (m, 2H; 6‐H, 7‐H), 7.46 to 7.49 ppm (m, 2H; 5‐H,
‐H); C NMR (100 MHz, CD Cl ): δ = 12.5 (d; Si‐CH),
7.4 (q; Me), 100.0 (s; C‐1, C‐4), 118.9 (d; C‐5, C‐8),
26.6 (d; C‐6, C‐7), 138.0 (s; C‐2, C‐3), 139.2 ppm (s;
0 minutes afforded the title compound with a conversion
13
2
2
1
H NMR (500 MHz, CD Cl ): δ = 3.33 (t, 6H; Me), 3.96
2
2
to 4.08 (q, 4H, O‐CH ) 7.04 (s, 2H; 2‐H, 3‐H), 7.25 to 7.28
2
C‐4a, C‐8a); HRMS (ESI‐Q‐TOF): m/z calcd for
C H O Si: 505.3169 [M + H ]; found: 505.3145.
(
m, 2H; 6‐H, 7‐H), 7.39 to 7.42 ppm (m, 2H; 5‐H, 8‐H);
+
28 49 4
1
3
C NMR (100 MHz, CD Cl ): δ = 15.4 (q; Me), 62.0 (t;
2
2
O‐CH ), 102.0 (s; C‐1, C‐4), 119.0 (d; C‐5, C‐8), 126.8 (d;
C‐6, C‐7), 134.2 (d; C‐2, C‐3), 137.5 ppm (s; C‐4a, C‐8a).
2
2.3.9 | 1,4‐Bis‐(1‐O‐2,3,4,6‐tetra‐O‐acetyl‐β‐D‐
glucopyranosyl)‐1,4‐dihydro‐1,4‐
epidioxidonaphthalene (2m)
2
.3.4 | 1,4‐Diisopropoxy‐1,4‐dihydro‐1,4‐
Reaction of naphthalene (1m, 123 mg, 0.15 mmol) for
epidioxidonaphthalene (2h)
2
40 minutes afforded the title compound with a conversion
of 99%.
Reaction of naphthalene 1h (37 mg, 0.15 mmol) for
1
H NMR (500 MHz, CD Cl ): δ = 1.93 (s, 3H; OAc),
2
2
3
0 minutes afforded the title compound with a conversion
1
.99 (s, 3H; OAc), 1.99 (s, 3H; OAc), 2.00 (s, 6H; OAc),
2.00 (s, 3H; OAc), 2.05 (s, 3H; OAc), 2.06 (s, 3H; OAc),
.84 (ddd, J = 10.0, 4.7, 2.1 Hz, 1H; 5‐H), 3.88 (ddd,
J = 10.1, 3.8, 2.4 Hz, 1H; 5’‐H), 4.01 (dd, J = 12.5,
.4 Hz, 1H; 6a’‐H), 4.06 (dd, J = 12.5, 2.1 Hz, 1H; 6a‐H),
4.28 (m, 2H; 6b‐H, 6b′‐H), 5.11 to 5.31 (m, 8H; 1‐H, 2‐H,
‐H, 4‐H); 6.94 (d, J = 9.3 Hz, 1H; ArH‐2/3), 7.16 (d,
of 99%.
1
H NMR (500 MHz, CD Cl ): δ = 1.28 (d, J = 6.1 Hz,
2
2
3
3
H; Me), 1.32 (d, J = 6.1 Hz, 3H; Me), 4.43 (sept,
J = 6.1 Hz, 2H; O‐CH), 6.99 (s, 2H; 2‐H, 3‐H), 7.23 to
2
7
8
.27 (m, 2H; 6‐H, 7‐H), 7.38 to 7.41 ppm (m, 2H; 5‐H,
13
‐H); C NMR (100 MHz, CD Cl ): δ = 23.4 (q; Me), 24.7
2
2
3
(
q; Me), 70.8 (d; O‐CH), 102.7 (s; C‐1, C‐4), 119.0 (d; C‐5,
C‐8), 126.7 (d; C‐6, C‐7), 135.2 (d; C‐2, C‐3), 137.7 ppm
s; C‐4a, C‐8a).
J = 9.3 Hz, 1H; ArH‐2/3), 7.28 to 7.33 (m, 2H; ArH‐6,
ArH‐7), 7.35 to 7.39 (m, 1H; ArH‐5/8), 7.43 to 7.46 (m,
(
13
1
H; ArH‐5/8); C NMR (100 MHz, CD Cl ): δ = 20.6 (q;
2
2
2
x OAc), 20.6 (q; 3 x OAc), 20.7 (q; 2 x OAc), 20.7 (q;
OAc), 61.0 (t; C‐6/6′), 61.1 (t; C‐6/6′), 66.5 (d; ), 66.8
d; ), 69.4 (d; ), 70.1 (d; ), 70.9 (d; ), 71.2 (d; ), 71.5 (d; ),
1.6 (d; ), 96.5 (d; C‐1), 101.7 (s; C‐1/4), 102.8 (s; C‐1/4),
119.2 (d; C‐5/8), 119.4 (d; C‐5/8), 127.5 (d; C‐6/7), 127.6 (d;
C‐6/7), 133.3 (s; C‐4a/8a), 135.5 (d; C‐2/3), 135.9 (s; C‐4a/
2
.3.5 | 1,4‐Diacetoxy‐1,4‐dihydro‐1,4‐
(
7
epidioxidonaphthalene (2i)
Photooxygenation of naphthalene 1i (37 mg, 0.15 mmol)
gave even after 600 minutes no conversion.