9788
M.P. Shurygina et al. / Tetrahedron 64 (2008) 9784–9788
5
75, 665, 730, 765, 780, 860, 870, 940, 1000, 1025, 1015, 1115, 1165,
1210, 1225, 1250, 1275, 1300, 1330, 1370, 1380, 1410, 1465, 1485,
ꢁ
1
1610, 1645, 1660, 1675, 1695 cm
;
d
H
(200 MHz, C
(50 MHz, C ) 197.59 (C]O), 154.91
O), 32.31 (CMe ),
6 6
D ) 3.10 (4H, s,
CH
2
O), 1.47 (18H, s, CMe
3
);
d
C
6 6
D
Acknowledgements
(
C(2) and C(5)), 108.80 (C(3) and C(4)), 64.77 (CH
2
3
3
3
0.42 (CMe ).
This study was financially supported by the Council on Grants of
President of the Russian Federation (Program for State Support of
Leading Scientific Schools of the Russian Federation, Grant
NSh-4947.2006.3) and the Russian Foundation for Basic Research
3.1.6. 4,6-Di-tert-butyl-5H-cyclopenta-1,3-dithiole-2,5-dione (2f)
Described in Ref. 28.
(
9
Project Nos. 06-03-33061-a, 07-03-00711, 08-03-01045-a, 08-03-
7055-r).
3
.1.7. 5,7-Di-tert-butyl-2,3-dihydro-6H-1,4-
ethanocyclopentapyrazin-6-one (2g)
ꢂ
Orange crystals, mp¼139–141 C. [Found: C, 74.26; H, 9.53; N,
References and notes
10.19%. C17
26 2
H N O requires: C, 74.41; H, 9.55; N, 10.21; O, 5.83%].
n
max(liquid film) 600, 660, 675, 740, 790, 810, 815, 850, 880,
1. El’zov, A. V.; Studzin’skii, O. P.; Grebenkina, V. M. Usp. Khim. 1977, 46, 185–227.
9
30, 955, 990, 1040, 1050, 1195, 1225, 1280, 1300, 1315, 1345, 1350,
2. Maier, G.; Franz, L. H.; Hartan, H.-G.; Lanz, K.; Reisernauer, H. Chem. Ber. 1985,
118, 3196–3204.
ꢁ1
1365, 1380, 1465, 1650, 1715 cm
;
d
H
(200 MHz, C
6 6
D ) 2.43–2.65
3. Vol’eva, V. B.; Ershov, V. V.; Belostozkaya, I. S.; Komisarova, N. L. Bull. Acad. Sci.
(
8H, m, CH N),1.43 (18H, s, CMe );
2
3
d
C
(50 MHz, C ) 202,58 (C]O),
6 6
D
USSR, Div. Chem. Sci. 1974, 739.
1
3
59.61 (C(2) and C(5)), 122.07 (C(3) and C(4)), 30.20 (CMe
2.40 (CMe ).
3
3
),
4. Vol’eva, V. B.; Belostozkaya, I. S.; Komisarova, N. L.; Starikova, Z. A.; Kurkov-
skaya, L. N. Zh. Org. Khim. 2006, 42, 243–245.
5
. Kliment’eva, S. V.; Mischenko, O. G.; Kurskii, Yu. A.; Faerman, V. I.; Maslennikov,
S. V.; Spirina, I. V.; Fukin, G. K.; Druzkov, N. O. Zh. Org. Khim. 2007, 77, 967–973.
. Imbriglio, J. E.; Rainier, J. D. Tetrahedron Lett. 2001, 42, 6987–6990.
6
3
.2. Photochemical conversion of 4,5-di-methoxy-3,6-di-tert-
7. McDonnell Bushnell, L. P.; Evitt, E. R.; Bergman, R. G. J. Organomet. Chem. 1978,
57, 445–446.
. Gesing, E. R. F.; Tane, J. P.; Vollhardt, K. P. C. Angew. Chem., Ind. Ed. 1980, 19,
023–1024.
9. Pearson, A. J.; Shively, R. J., Jr.; Dubbert, R. A. Organometallics 1992,11, 4096–4104.
0. Pearson, A. J.; Shively, R. J., Jr.; Dubbert, R. A. Organometallics 1994, 13, 578–584.
1. Mauthner, K.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 1994, 13,
054–5061.
12. Slugove, C.; Mauthner, K.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics
996, 15, 2954–2960.
3. Washington, J.; McDonald, R.; Takats, J.; Menashe, N.; Reshef, D.; Shvo, Y.
1
butyl-o-benzoquinone
8
1
The irradiation (284 K, light
l>520 nm for 100 h) of benzene
1
1
solution of 1d was carried out using procedure described earlier.
The solvent (benzene) was removed under reduced pressure
without heating. The solid residue was washed with cold hexane
and recrystallized from diethylether. Colourless rhombic crystals
of 2,3a,6,8-tetra-tert-butyl-1,9,9a,9b-tetra-methoxy-9a,9b-di-hydro-
5
1
1
Organometallics 1995, 14, 3996–4003.
cyclopentachromene-3,4,7-(3aH)-trione (4) were isolated with
14. Tamao, K.; Kohayashi, K.; Ito, Y. Synlett 1992, 539–542.
15. Einfuhrung in die photochemie, Von einem autorenkollektiv; Bekker, G. O., Ed.;
VEB Deutscher Verlag der Wissenschaften: Berlin, 1976; p 379.
ꢂ
w20% yield. Mp¼200–203 C. [Found: C, 67.79; H, 8.84%. C32
48 8
H O
requires: C, 67.86; H, 8.82; O, 23.33%];
30, 840, 870, 885, 930, 950, 9650, 1000, 1020, 1055, 1075, 1095,
130, 1160, 1170, 1185, 1210, 1225, 1260, 1270, 1320, 1370, 1380,
nmax(liquid film) 670, 720,
1
6. Chesnokov, S. A.; Cherkasov, V. K.; Abakumov, G. A.; Kurskii, Yu. A.; Shurygina,
M. P.; Mamysheva, O. N.; Shavyrin, S. A. Russ. Chem. Bull., Int. Ed. 2003, 3,
18–724.
7
7
1
ꢁ
1
17. Chesnokov, S. A.; Cherkasov, V. K.; Chechet, Yu. V.; Nevodchikov, V. I.; Abaku-
mov, G. A.; Mamysheva, O. N. Russ. Chem. Bull., Int. Ed. 2000, 9, 1506–1511.
18. Shurygina, M. P.; Kurskii, Yu. A.; Chesnokov, S. A.; Druzkov, N. O.; Fukin, G. K.;
Abakumov, G. A.; Cherkasov, V. K. Russ. Chem. Bull., Int. Ed. 2006, 55, 1585–1592.
1400, 1470, 1610, 1630, 1650, 1710, 1790 cm
;
d
H
(200 MHz, C
), 2.89 (6H, s, OCH ), 1.58 (9H, s,
), 1.45 (9H, s, CMe ), 1.35 (9H, s, CMe );
3
) 196.3 (C]O), 190.6 (C]O), 174.7 (O–C]O), 131.1,
6 6
D )
3
CMe
(
.68 (3H, s, OCH
), 1.52 (9H, s, CMe
50 MHz, CDCl
3
), 3.37 (3H, s, OCH
3
3
3
3
3
3
d
C
19. Kropp, P. J. In Organic Photochemistry; Chapman, O. L., Ed.; Marcel Dekker: New
York, NY, 1967; Vol. 1, pp 125–131.
135.5, 138.1, 150.3, 157.1, 163.2 (C(1), C(2), C(5a), C(6), C(8), C(9)),
20. Dauben, W. G.; Spitzer, W. A.; Kellogg, M. S. J. Am. Chem. Soc. 1971, 93, 3674–
7
2.1, 82.3, 92.3 (C(3a), C(9a), C(9b)), 159.61 (C(2) and C(5)), 64.6
3677.
2
2
2
1. Zimmerman, H. E. Photochemistry 1963, 1, 183–185.
2. Zimmerman, H. E. Angew. Chem., Int. Ed. Engl. 1969, 1, 1–11.
3. Barton, D. H. R.; de Mayo, P.; Shafiq, M. J. Chem. Soc. 1958, 3314–3315.
(OCH
CMe
3
), 61.4 (OCH
3
), 57.6 (OCH
3
3
), 51.8 (OCH ), 38.3, 36.1, 35.9
(
3
), 32.8, 31.0, 30.4, 29.5 (CCH
3
).
The hexane solution contains 1,3-di-tert-butyl-4,5-di-methoxy-
24. Hixson, S. S.; Mariano, P. S.; Zimmerman, H. E. Chem. Rev. 1973, 73, 531–551.
25. Barltrop, J. A.; Coyle, J. D. Excited States in Organic Chemistry; John Wiley and
Sons: London, New York, NY, Sydney, Toronto, 1975; p 446.
1
bicyclo[3.1.0]hex-3-ene-2,6-dione (3) and 2d in the ratio 1:2. H NMR
of compound 3: (200 MHz, C ) 3.53 (3H, s, OCH ), 3.16 (3H, s,
OCH ), 1.23 (9H, s, CMe ), 1.13 (9H, s, CMe ); (50 MHz, C
96.31 (C]O), 188.26 (C]O), 179.5 (C(5)), 138.36 (C(4)), 94.56
OCH ), 57.9 (C(3)), 51.4 (C(2)), 31.3 (CMe ), 30.9 (CMe ), 30.3
CMe ), 27.9 (CMe ).
The crystals of 4 suitable for X-ray structure determination were
obtained from ether. Crystal data: C32
, M¼560.72, mono-
clinic, a¼10.894(4) b¼22.695(8), c¼12.240(4) Å, ¼98.883(7),
d
H
6
D
6
3
2
2
2
2
3
6. Coyle, J. D. Introduction to Organic Photochemistry; John Wiley and Sons: Lon-
don, 1989; p 176.
7. Cowan, D. O.; Drisko, R. L. Elements of Organic Photochemistry; John Wiley and
Sons: London, New York, NY, 1976; p 586.
8. Kuropatov, V. A.; Cherkasov, V. K.; Kurskii, Yu. A.; Fukin, G. K.; Abakumova, L. G.;
Abakumov, G. A. Russ. Chem. Bull., Int. Ed. 2006, 4, 708–711.
9. Garnov, V. A.; Nevodchikov, V. I.; Abakumov, G. A.; Abakumova, L. G.; Kurskii,
Yu. A.; Cherkasov, V. K. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1985, 34, 2589–2591.
0. Abakumov, G. A.; Cherkasov, V. K.; Abakumova, L. G.; Nevodchikov, V. I. Bull.
Acad. Sci. USSR, Div. Chem. Sci. 1990, 39, 984–986.
3
3
3
d
C
6 6
D )
1
(
(
3
3
3
3
3
48 8
H O
b
3
V¼2989.9(18) Å , T¼100(2)K, space group P2(1)/n, Z¼4,
31. Abakumov, G. A.; Cherkasov, V. K.; Abakumova, L. G.; Nevodchicov, V. I.;
ꢁ
1
3
Druzhkov, N. O.; Makarenko, N. P.; Kursky, Ju. A. J. Organomet. Chem. 1995, 491,
m
6
R
¼0.088 mm , dcal¼1.246 g/cm , 28,770 reflections measured,
127–133.
853 unique (Rint¼0.0232), which were used in all calculations.
32. Abakumov, G. A.; Cherkasov, V. K.; Abakumova, L. G.; Druzhkov, N. O.; Ne-
vodchicov, V. I.; Kursky, Ju. A.; Makarenko, N. P. Metalloorg. Khim. 1991, 4, 683–
686.
1
[I>2
s
(I)]¼0.0445,
wR
2
¼0.1186,
wR
1
(all
data)¼0.0522,
2
GOF(F )¼1.050. The structure was solved by direct method and
refined on F2 using SHELXTL package. The H atoms were found
from Fourier syntheses and refined isotropically.
33. Garnov, V. A.; Nevodchikov, V. I.; Abakumova, L. G.; Abakumov, G. A.; Cher-
35
kasov, V. K. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1987, 36, 1728–1730.
34. Abakumov, G. A.; Cherkasov, V. K.; Kocherova, T. N.; Druzkov, N. O.; Kurskii, Yu.
A.; Bubnov, M. P.; Fukin, G. K.; Abakumova, L. G. Russ. Chem. Bull., Int. Ed. 2007,
56, 1849–1856.
35. Sheldrick, G. M. SHELXTL v. 6.12, Structure Determination Software Suite; Bruker
AXS: Madison, WI, USA, 2000.