7940
N. Hoffmann / Tetrahedron 58 (2002) 7933–7941
Luyten, I.; Sandra, P.; Hoornaert, G.; Van der Eycken, E. Org.
11. Hoffmann, N.; Pete, J. P. J. Org. Chem. 1997, 62, 6952–6960.
12. For the influence of acidic media in similar reactions see:
(a) Kalena, G. P.; Pradhan, P.; Banerji, A. Tetrahedron Lett.
1992, 55, 7775–7778. (b) Kalena, G. P.; Pradhan, P.; Banerji,
A. Tetrahedron 1999, 55, 3209–3218. (c) Ohkura, K.;
Kanazashi, N.; Seki, K. Chem. Pharm. Bull. 1993, 41,
239–243. (d) Ohkura, K.; Seki, K.; Hiramatsu, H.; Aoe, K.;
Terashima, M. Heterocycles 1997, 44, 467–478. (e) Ohkura,
K.; Noguchi, Y.; Seki, K. Heterocycles 1998, 47, 429–437.
(f) Howell, N.; Pincock, J. A.; Stefanova, R. J. Org. Chem.
2000, 65, 6173–6178. (g) Matohara, K.; Lim, C.; Yasutake,
M.; Nogita, R.; Koga, T.; Sakamoto, Y.; Shinmyozu, T.
Tetrahedron Lett. 2000, 41, 6803–6807. (h) Mallory, F. B.;
Mallory, C. W. Org. React. 1983, 30, 1–456. (i) Mori, T.;
Wada, T.; Inoue, Y. Org. Lett. 2000, 2, 3401–3404. (j) Ho,
T.-I.; Ho, J.-H.; Wu, J. Y. J. Am. Chem. Soc. 2000, 122,
8575–8576. (k) Ho, J.-H.; Ho, T.-I.; Liu, R. S. H. Org. Lett.
2001, 3, 409–411. (l) Schultz, A. G.; Antoulinakis, E. G.
J. Org. Chem. 1996, 61, 4555–4559. (m) Chow, Y. L.; Liu, X.
Can. J. Chem. 1991, 69, 1261–1272.
Lett. 2001, 3, 1173–1175. (o) Wender, P. A.; Ternansky, R.;
deLong, M.; Singh, S.; Olivero, A.; Rice, K. Pure Appl. Chem.
1990, 62, 1597–1602. (p) Wender, P. A.; Siggel, L.; Nuss,
J. M. Comprehensive Organic Synthesis; Trost, B. M.,
Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991;
Vol. 5, pp 645–673. (q) Wender, P. A.; Siggel, L.; Nuss, J. M.
Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker:
New York, 1989; Vol. 10, pp 357–473. (r) Wender, P. A.;
Dore, T. M. In CRC Handbook of Photochemistry and
Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC:
Boca Raton, 1995; pp 280–290.
2. (a) Bryce-Smith, D.; Gilbert, A.; Orger, B.; Tyrrell, H.
J. Chem. Soc., Chem. Commun. 1974, 334–336. (b) Leismann,
H.; Mattay, J.; Scharf, H. D. J. Am. Chem. Soc. 1984, 106,
3985–3991. (c) Mattay, J.; Runsink, J.; Gersdorf, J.;
Rumbach, T.; Ly, C. Helv. Chim. Acta 1986, 69, 442–455.
(d) Mu¨ller, F.; Mattay, J. Chem. Rev. 1993, 93, 99–117.
3. Cornelisse, J. Chem. Rev. 1993, 93, 615–669.
´ ´
´
4. Vızvardi, K.; Toppet, S.; Hoornaert, G. J.; De Keukeleire, D.;
Bako, P.; Van der Eycken, E. J. Photochem. Photobiol. A:
13. (a) De Schryver, F. C.; Boens, N.; Put, J. Advances in
Photochemistry; Pitts, J. N.; Jr., Hammond, G. S., Gollnick,
K., Eds.; Wiley: New York, 1977; Vol. 10, pp 359–463.
(b) Davidson, R. S. Advances in Physical Organic Chemistry;
Gold, V., Bethell, D., Eds.; Academic: London, 1983; Vol. 19,
pp 1–130.
Chem. 2000, 133, 135–146. (b) Van der Eycken, E.; De
Keukeleire, D.; De Bruyn, A. Tetrahedron Lett. 1995, 36,
3573–3576. (c) De Keukeleire, D. Aldrichim. Acta 1994, 27,
59–69. (d) De Keukeleire, D.; He, S.-L.; Blakemore, D.;
Gilbert, A. J. Photochem. Photobiol. A.: Chem. 1994, 80,
233–240. (e) Gilbert, A.; Taylor, G. N.; bin Samsudin, M. W.
J. Chem. Soc., Perkin Trans. 1 1980, 869–876. (f) Mattay, J.;
Leismann, H.; Scharf, H. D. Chem. Ber. 1979, 112, 577–599.
(g) Kishikawa, K.; Akimoto, S.; Kohmoto, S.; Yamamoto, M.;
Yamada, K. J. Chem. Soc., Perkin Trans. 1 1997, 77–84.
(h) Mani, J.; Schu¨ttel, S.; Zhang, C.; Bigler, P.; Mu¨ller, C.;
Keese, R. Helv. Chim. Acta 1989, 72, 487–495. (i) Cornelisse,
J.; de Haan, R. Molecular and Supramolecular Photo-
chemistry; Ramamuthy, V., Schanze, K. S., Eds.; Marcel
Dekker, New York, 2001; Vol. 8, pp 1–126. (j) Mizuno, K.;
Maeda, H.; Sugimoto, A.; Chiyonobu, K. Molecular and
Supramolecular Photochemistry; Ramamuthy, V., Schanze,
K. S., Eds.; Marcel Dekker, New York, 2001; Vol. 8,
pp 127–241. (k) Wagner, P. J. Acc. Chem. Res. 2001, 34,
1–8. (l) De Keukeleire, D.; He, S.-L. Chem. Rev. 1993, 93,
359–380.
14. (a) McCullough, J. J. Chem. Rev. 1987, 87, 811–860.
¨
¨
(b) Dopp, D.; Memarian, H. R.; Kruger, C.; Raabe, E.
¨
Chem. Ber. 1989, 122, 585–588. (c) Dopp, D.; Memarian,
¨
H. R. Chem. Ber. 1990, 123, 315–319. (d) Dopp, D.; Erian,
A. W.; Henkel, G. Chem. Ber. 1993, 126, 239–242.
¨
(e) Lanfermann, H.; Dopp, D. J. Inform. Rec. Mats. 1994,
21, 545–547. (f) Memarian, H. R.; Nasr-Esfahani, M.; Boese,
¨
R.; Dopp, D. Liebigs Ann./Receuil 1997, 1023–1027.
¨
(g) Memarian, H. R.; Nasr-Esfahani, M.; Dopp, D. New
J. Chem. 2001, 25, 476–478. (h) Memarian, H. R.; Nasr-
¨
Esfahani, M.; Dopp, D. New J. Chem. 2001, 25, 1605–1609.
(i) Al-Jalal, N. A. J. Chem. Res. (S) 1995, 44. (j) Al-Jalal,
N. A.; Prichard, R. G.; McAuliffe, C. A. J. Chem. Res. (S)
1994, 452. (k) Mizuno, K.; Konishi, S.; Yoshimi, Y.;
Sugimoto, A. Chem. Commun. 1998, 1659–1660.
(l) Yokohama, A.; Mizuno, K. Org. Lett. 2000, 2,
3457–3459. (m) Wagner, P. J.; Sakamoto, M. J. Am. Chem.
Soc. 1989, 111, 9254–9256. (n) Noh, T.; Kim, D.; Kim, Y.-J.
J. Org. Chem. 1998, 63, 1212–1216, see also Ref. 4j.
15. Hoffmann, N.; Pete, J. P.; Inoue, Y.; Mori, T. J. Org. Chem.
2002, 67, 2315–2322.
5. (a) Bryce-Smith, D.; Gilbert, A. Tetrahedron 1976, 32,
1309–1326. (b) Bryce-Smith, D.; Gilbert, A. Tetrahedron
1977, 33, 2459–2490. (c) Houk, K. N. Pure Appl. Chem. 1982,
54, 1633–1650. (d) van der Hart, J. A.; Mulder, J. J. C.;
Cornelisse, J. J. Mol. Struct. (Theochem) 1987, 151, 1–10.
(e) van der Hart, J. A.; Mulder, J. J. C.; Cornelisse, J.
J. Photochem. Photobiol. A: Chem. 1991, 61, 3–13.
(f) Stehouwer, A. M.; van der Hart, J. A.; Mulder, J. J. C.;
Cornelisse, J. J. Mol. Struct. (Theochem.) 1992, 92, 333–338.
(g) van der Hart, J. A.; Mulder, J. J. C.; Cornelisse, J.
J. Photochem. Photobiol. A: Chem. 1995, 86, 141–148.
6. Clifford, S.; Bearpark, M. J.; Bernardi, F.; Olivucci, M.; Robb,
M. A.; Smith, B. R. J. Am. Chem. Soc. 1996, 118, 7353–7360.
7. Hoffmann, N.; Pete, J. P. Tetrahedron Lett. 1995, 36,
2623–2626.
16. (a) Grivens, R. R. Organic Photochemistry; Padwa, A., Ed.;
Marcel Dekker, Inc: New York, 1981; Vol. 5, pp 227–346.
(b) Criegee, R. Chimia 1968, 22, 392–396.
17. (a) Dickinson, R. G.; Jacobsen, N. W. Chem. Commun. 1970,
1719–1720. (b) Hopps, H. B. Aldrichim. Acta 2000, 33,
28–30.
18. Triplet energies: E-piperylene: 247 kJ/mol; Z-piperylene:
240 kJ/mol; Z-b-methylstyrene(comparable with 3): 275 kJ/
mol; acetone: 332 kJ/mol, see: Murov, S. L.; Carmichael, I.;
Hug, G. L. Handbook of Photochemistry; Marcel Dekker, Inc:
New York, 1993.
8. Hoffmann, N.; Pete, J. P. Synthesis 2001, 1236–1242.
9. Hoffmann, N.; Pete, J. P. Tetrahedron Lett. 1998, 39,
5027–5030.
19. Numao, N.; Hamada, T.; Yonemitsu, O. Tetrahedron Lett.
1977, 1661–1664.
10. (a) Hoffmann, N.; Pete, J. P. Tetrahedron Lett. 1996, 37,
2027–2030. (b) Verrat, C.; Hoffmann, N.; Pete, J. P. Synlett
2000, 1166–1168.
20. 1,2-Hydrogene shifts are not so frequently observed in similar
cases. For comparable examples see: (a) Kharasch, M. S.;
Weiner, M.; Nudenberg, W.; Bhattacharya, A.; Wang, T.-I.;