Strained allenes as dienophiles in the Diels-Alder reaction: An experimental and computational study

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 976-983

  Nendel, Maja ^a,b   Tolbert, Laren M ^a   Herring, Laura E ^a   Islam, Md Nurul ^c   Houk, K N ^b  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c Bangladesh Institute of Technology   (Bangladesh)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

EID: 0033525196     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982091c     Document Type: Article

References (52)

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18. (a) The use of allene and fluoroallenes as dienophiles in Diels- Alder reactions has been studied by semiempirical methods: Manohan, M.; Venuvanalingam, P. J. Chem. Soc., Perkin Trans. 2 1996, 1423. (b) The [2 + 2] and [2 + 4] reactivity of heterocumulenes and ketenes was studied: Fabian, W. M. F.; Janoschek, R. J. Am. Chem. Soc. 1997, 119, 4253. (c) Salzner, U.; Bachrach, S. M. J. Org. Chem. 1996, 61, 237. (e) The reactivity of strained allenes in [2 + 2] cycloadditions was also studied: Burrell, R, C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
19. (a) The use of allene and fluoroallenes as dienophiles in Diels- Alder reactions has been studied by semiempirical methods: Manohan, M.; Venuvanalingam, P. J. Chem. Soc., Perkin Trans. 2 1996, 1423. (b) The [2 + 2] and [2 + 4] reactivity of heterocumulenes and ketenes was studied: Fabian, W. M. F.; Janoschek, R. J. Am. Chem. Soc. 1997, 119, 4253. (c) Salzner, U.; Bachrach, S. M. J. Org. Chem. 1996, 61, 237. (e) The reactivity of strained allenes in [2 + 2] cycloadditions was also studied: Burrell, R, C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
20. (a) The use of allene and fluoroallenes as dienophiles in Diels- Alder reactions has been studied by semiempirical methods: Manohan, M.; Venuvanalingam, P. J. Chem. Soc., Perkin Trans. 2 1996, 1423. (b) The [2 + 2] and [2 + 4] reactivity of heterocumulenes and ketenes was studied: Fabian, W. M. F.; Janoschek, R. J. Am. Chem. Soc. 1997, 119, 4253. (c) Salzner, U.; Bachrach, S. M. J. Org. Chem. 1996, 61, 237. (e) The reactivity of strained allenes in [2 + 2] cycloadditions was also studied: Burrell, R, C.; Daoust, K. J.; Bradley, A. Z.; DiRico, K. J.; Johnson, R. P. J. Am. Chem. Soc. 1996, 118, 4218.
21. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 117, 6036.
22. (a) E.g., the vinylcyclopropane rearrangement: Houk, K. N.; Nendel, M.; Wiest, O.; Storer, J. W. J. Am. Chem. Soc. 1997, 119, 10545. (b) As well as the Cope and Claisen rearrangements: Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
23. (a) E.g., the vinylcyclopropane rearrangement: Houk, K. N.; Nendel, M.; Wiest, O.; Storer, J. W. J. Am. Chem. Soc. 1997, 119, 10545. (b) As well as the Cope and Claisen rearrangements: Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
24. Benson, S. W. Thermochemical Kinetics. Methods for Estimation of Thermochemical Data and Rate Parameters, 2nd ed.; Wiley: New York, 1976.
25. Endo and exo refer to the position of the diene relative to the former cyclohexadiene, rather than to the position of the substituent on the ring.
26. (a) Gruber, L.; Tömösközi, I.; Radics, L. Synthesis 1976, 708.
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29. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
30. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
31. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
32. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
33. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
34. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
35. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
36. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
37. E.g., the reaction of cyclopentadiene with (-)-menthyl acrylate: (a) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 6359. (b) Sauer, J.; Kredel, J. Angew. Chem. 1965, 77, 1037; Angew. Chem., Int. Ed. Engl. 1965, 4, 989. (c) Farmer, R. F.; Hamer, J. J. Org. Chem. 1966, 31, 2418. (d) Sauer, J.; Kredel, J. Tetrahedron Lett. 1966, 731. Or the reaction of butadiene with di-(-)-menthyl fumerate: (e) Korolev, A.; Mur, V. Dokl. Akad. Nauk USSR 1948, 59, 251. (f) Korolev, A.; Mur, V. Chem. Abstr. 1948, 42, 6776. (g) Walborsky, H. M.; Barash, L.; Davis, T. C. Tetrahedron 1963, 19, 2333. (h) Walborsky, H. M.; Barash, L.; Davis, T. C. J. Org. Chem. 1961, 26, 4778.
38. Gaussian 94 (Revision B.1): Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L., Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
39. (a) Yamaguchi, K.; Jensen, F.; Dorigo, A.; Houk, K. N. Chem. Phys. Lett. 1988, 149, 537.
40. (b) Yamakami, S.; Kawakami, T.; Nagao, H.; Yamaguchi, K. Chem. Phys. Lett. 1994, 231, 25.
41. (a) MM2* is a modified version of Allinger's MM2 force field: Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127. (b) MACROMODEL V5: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
42. (a) MM2* is a modified version of Allinger's MM2 force field: Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127. (b) MACROMODEL V5: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
43. (a) The reaction of ethylene and butadiene is exothermic by 36.6 kcal/mol (ref 8). (b) The experimental barrier of the reaction of 1,3- butadiene and ethylene is 25.1 ± 2 kcal/mol: Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. 1991, 104, 711; Angew. Chem., Int. Ed. Engl. 1991, 31, 682. (c) The experimental heat of formation is 38.5 kcal/mol: Uchiyama, M.; Tomioka, T.; Amano, A. J. Phys. Chem. 1964, 68, 1878.
44. (a) The reaction of ethylene and butadiene is exothermic by 36.6 kcal/mol (ref 8). (b) The experimental barrier of the reaction of 1,3-butadiene and ethylene is 25.1 ± 2 kcal/mol: Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. 1991, 104, 711; Angew. Chem., Int. Ed. Engl. 1991, 31, 682. (c) The experimental heat of formation is 38.5 kcal/mol: Uchiyama, M.; Tomioka, T.; Amano, A. J. Phys. Chem. 1964, 68, 1878.
45. (a) The reaction of ethylene and butadiene is exothermic by 36.6 kcal/mol (ref 8). (b) The experimental barrier of the reaction of 1,3- butadiene and ethylene is 25.1 ± 2 kcal/mol: Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. 1991, 104, 711; Angew. Chem., Int. Ed. Engl. 1991, 31, 682. (c) The experimental heat of formation is 38.5 kcal/mol: Uchiyama, M.; Tomioka, T.; Amano, A. J. Phys. Chem. 1964, 68, 1878.
46. (a) The reaction of ethylene and butadiene is exothermic by 36.6 kcal/mol (ref 8). (b) The experimental barrier of the reaction of 1,3- butadiene and ethylene is 25.1 ± 2 kcal/mol: Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem. 1991, 104, 711; Angew. Chem., Int. Ed. Engl. 1991, 31, 682. (c) The experimental heat of formation is 38.5 kcal/mol: Uchiyama, M.; Tomioka, T.; Amano, A. J. Phys. Chem. 1964, 68, 1878.
47. Since the propadiene moiety is at the "inside" of the former butadiene, it is referred to as "gauche-in".
48. 2) ≈ 1.
49. Geometry optimizations starting with either an anti or a gauche-out conformation about the newly formed bond provide the structure of Figure 3.
50. In the case of cyclopentene, a typical example for a molecule with an envelope conformation, the ring flip requires only 0.8 kcal/ mol: Cavagnat, D.;Roberts, M. P.; Cavagnat, R. M.; Vahedi-Banisaeid, S. J. Phys. Chem. 1991, 95, 134.
51. This is the lowest energy conformer. The other conformers are located within 1.7 kcal/mol above it.
52. Eksterowicz, J. E.; Houk, K. N. Chem. Rev. 1993, 93, 2439.