Gold(III) Chloride-Catalyzed Addition Reactions of Electron-Rich Arenes to Methyl Vinyl Ketone

Advanced Synthesis and Catalysis

Volumn 345, Issue 11, 2003, Pages 1247-1252

  Dyker, Gerald ^a   Muth, Enrico ^a   Hashmi, A Stephen K ^b   Ding, Li ^b  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Acids; Aromatic substitution; Gold; Homogeneous catalysis; Lewis acids; Michael acceptors

Indexed keywords

GOLD CHLORIDE; KETONE DERIVATIVE; METHYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON; VINYL DERIVATIVE;

ADDITION REACTION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION; METALLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0347594386     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303098     Document Type: Article

References (37)

1. J. Tsuji, H. Nagashima, Tetrahedron 1984, 40, 2699-2702.
2. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992-1995.
3. K. B. Jensen, J. Thorauge, R. G. Hazell, K. A. Jorgensen, Angew. Chem. 2001, 113, 164-167; Angew. Chem. Int. Ed. 2001, 40, 160-163.
4. K. B. Jensen, J. Thorauge, R. G. Hazell, K. A. Jorgensen, Angew. Chem. 2001, 113, 164-167; Angew. Chem. Int. Ed. 2001, 40, 160-163.
5. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
6. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
7. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
8. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
9. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
10. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
11. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
12. A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385; Angew. Chem. Int. Ed. 2000, 39, 2285-2288; A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771; A. S. K. Hashmi, T. M. Frost, J. W. Bats, Catal. Today 2002, 72, 19-27; J. W. Dankwardt, Tetrahedron Lett. 2001, 42, 5809-5812; N. Asao, K. Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc. 2002, 124, 12650-12651; A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
13. K. Alder, C.-H. Schmidt, Chem. Ber. 1943, 76, 183-205.
14. For the formation by the addition of HCl to MVK, see: A. Treibs, Angew. Chem. 1948, 60, 289-297; J. Decombe, C. R. Hebd. Seances Acad. Sci. 1936, 202, 1685-1687; L. I. Smith, J. A. Sprung; J. Am. Chem. Soc. 1943, 65, 1276-1283.
15. For the formation by the addition of HCl to MVK, see: A. Treibs, Angew. Chem. 1948, 60, 289-297; J. Decombe, C. R. Hebd. Seances Acad. Sci. 1936, 202, 1685-1687; L. I. Smith, J. A. Sprung; J. Am. Chem. Soc. 1943, 65, 1276-1283.
16. For the formation by the addition of HCl to MVK, see: A. Treibs, Angew. Chem. 1948, 60, 289-297; J. Decombe, C. R. Hebd. Seances Acad. Sci. 1936, 202, 1685-1687; L. I. Smith, J. A. Sprung; J. Am. Chem. Soc. 1943, 65, 1276-1283.
17. 4, see: T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4732.
18. G. Dujardin, J.-M. Poirier, Bull. Soc. Chim. Fr. 1994, 131, 900-909.
19. V. J. Bulbule, V. H. Deshpande, A. V. Bedekar, J. Chem. Res. Synop. 2000, 5, 220-221; J.-M. Poirier, G. Dujardin, Heterocycles 1987, 25, 399-407; G. Jenner, J. Rimmelin, F. Antoni, S. Libs, E. Schleiffer, Bull. Soc. Chim. Fr. 1981, 2, 65-70.
20. V. J. Bulbule, V. H. Deshpande, A. V. Bedekar, J. Chem. Res. Synop. 2000, 5, 220-221; J.-M. Poirier, G. Dujardin, Heterocycles 1987, 25, 399-407; G. Jenner, J. Rimmelin, F. Antoni, S. Libs, E. Schleiffer, Bull. Soc. Chim. Fr. 1981, 2, 65-70.
21. V. J. Bulbule, V. H. Deshpande, A. V. Bedekar, J. Chem. Res. Synop. 2000, 5, 220-221; J.-M. Poirier, G. Dujardin, Heterocycles 1987, 25, 399-407; G. Jenner, J. Rimmelin, F. Antoni, S. Libs, E. Schleiffer, Bull. Soc. Chim. Fr. 1981, 2, 65-70.
22. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
23. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
24. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
25. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
26. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
27. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
28. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
29. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
30. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
31. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
32. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
33. For spectroscopic data, see: P. Boudjouk, B.-K. Kim, B.-H. Han, Synth. Commun. 1996, 26, 3479-3484; F.-E. Chen, J.-D. Liu, H. Fu, Z.-Z. Peng, L.-Y. Shao, Synth. Commun. 2000, 30, 2295-2299; T. Kataoka, H. Kinoshita, T. Iwama, S.-i. Tsujiyama, T. Iwamura, S.-i. Watanabe, O. Muraoka, G. Tanabe, Tetrahedron 2000, 56, 4725-4731; T. Ibrahim, T. J. Grattan, J. S. Whitehurst, J. Chem. Soc. Perkin Trans. 1 1990, 3317-3319; K. Griesbaum, G. Kiesel, H. Mertens, P. Krieger-Beck, H. Henke, Can. J. Chem. 1994, 72, 2198-2204; G. Just, D. Crosilla, Can. J. Chem. 1980, 58, 2349-2357; B. M. Trost, R. A. Kunz, J. Am. Chem. Soc. 1975, 97, 7152-7157; J. Grignon, S. Fliszár, Can. J. Chem. 1974, 52, 3209-3217; E. Brown, J. Touet, M. Ragault, Bull. Soc. Chim. Fr. 1972, 212-220; E. Rothstein, D. J. Stanbank, R. Whiteley, J. Chem. Soc. C 1968, 746-752; G. Fierz, J. F. McGarrity, H. Dahn, Helv. Chim. Acta 1975, 58, 1058-1071; L. Simeral, G. E. Maciel, J. Phys. Chem. 1973, 77, 1590-1593.
34. W. Francke, W. Reith, Tetrahedron Lett. 1981, 22, 2029-2032.
35. M. A. Tobias, J. Org. Chem. 1970, 35, 267-269.
36. F. A. B. Aldous, B. C. Barrass, K. Brewster, D. A. Buxton, D. M. Green, R. M. Pinder, P. Rich, M. Skeels, K. J. Tutt, J. Med. Chem. 1974, 17, 1100-1111.
37. H. Kono, M. Ishige, K. Sakai, M. Shiga, I. Motoyama, K. Hata, Bull. Chem. Soc. Jpn. 1970, 43, 867-872.