On the behavior of α,β-unsaturated thioaldehydes and thioketones in the Diels-Alder reaction

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6601-6612

  Li, Guang Ming ^a,b   Niu, Shuqiang ^a,c   Segi, Masahito ^d   Tanaka, Koichiro ^d   Nakajima, Tadashi ^d   Zingaro, Ralph A ^a   Reibenspies, Joseph H ^a   Hall, Michael B ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b Research and Development Department   (Japan)

^c PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^d KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN DERIVATIVE; ALUMINUM DERIVATIVE; CARBONYL DERIVATIVE; CINNAMALDEHYDE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; NORBORNADIENE DERIVATIVE; PYRAN DERIVATIVE; SULFIDE; THIOALDEHYDE; THIOKETONE;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; CYCLIZATION; DIMERIZATION; MELTING POINT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS; THERMODYNAMICS;

ALDEHYDES; CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; DIMERIZATION; DISULFIDES; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NORBORNANES; SUPPORT, NON-U.S. GOV'T;

EID: 0012360361     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000740q     Document Type: Article

References (68)

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34. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
35. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
36. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
37. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
38. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
39. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
40. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
41. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
42. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
43. Selected references on thiabutadienes; Theoretical work: (a) Beslin, P.; Lagain, D.; Vialle, J.; Minot, C. Tetrahedron 1981, 37, 3839. (b) Yamabe, S.; Kawajiri, S.; Minato, T.; Machiguchi, T. J. Org. Chem. 1993, 58, 1122. Experimental work: (c) Pradere, J.-P.; Bouet, G.; Quiniou, H. Tetrahedron Lett. 1972, 3471. (d) Lipkowitz, K. B.; Mundy, B. P. Tetrahedron Lett. 1977, 3417. (e) Karakasa, T.; Motoki, S. J. Org. Chem. 1978, 43, 4147. (f) Karakasa, T.; Motoki, S. J. Org. Chem. 1979, 44, 4151. (g) Ohmura, H.; Motoki, S. Bull. Chem. Soc. Jpn. 1984, 57, 1131. (h) Motoki, S.; Saito, T.; Karakasa, T.; Matsushita, T.; Furuno, E. J. Chem. Soc., Perkin Trans. 1 1992, 2943. (i) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. J. Am. Chem. Soc. 1982, 104, 312. (j) Bock, H.; Mohmand, S.; Hirabayashi, T.; Semkow, A. Chem. Ber. 1982, 115, 1339. (k) Vedejs, E.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445. (l) Beslin, P. J. Heterocycl. Chem. 1983, 20, 1753. (m) Liao, L.-F.; Tseng, P.-W.; Chou, C.-H.; Chou, W.-C.; Fang, J.-M. Heterocycles 1995, 41, 1967. (n) Saito, T.; Takekawa, K.; Nishimura, J.; Kawamura, M. J. Chem. Soc., Perkin Trans. 1 1997, 2957. (o) Saito, T.; Takekawa, K.; Takahashi, T. Chem. Commun. 1999, 1001.
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