Corannulene. A three-step synthesis

Journal of the American Chemical Society

Volumn 119, Issue 45, 1997, Pages 10963-10968

  Scott, Lawrence T ^a   Cheng, Pei Chao ^a   Hashemi, Mohammed M ^b   Bratcher, Matthew S ^a   Meyer, Dayton T ^a   Warren, Hope B ^a  

^a BOSTON COLLEGE   (United States)

^b SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ACENAPHTHENE DERIVATIVE; ANNULENE DERIVATIVE;

ARTICLE; CYCLIZATION; PYROLYSIS; SYNTHESIS;

EID: 0030662640     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972019g     Document Type: Article

References (95)

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2. For earlier accounts of this work, see: (a) Meyer, D. M. S. Thesis, University of Nevada, Reno, 1991. (b) Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. (c) Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920-1. (d) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, Victoria, British Columbia, July, 1992, Abstract No. 64. (e) Cheng, P.-C. M. S. Thesis, University of Nevada, Reno, 1992. (f) Scott, L. T. International Symposium on Synthetic and Mechanistic Hydrocarbon Chemistry, Fukuoka, Japan, December 6-9, 1993, Abstract No. 7-A. (g) Cheng, P.-C. Ph.D. Dissertation, Boston College, 1996.
3. For earlier accounts of this work, see: (a) Meyer, D. M. S. Thesis, University of Nevada, Reno, 1991. (b) Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. (c) Scott, L. T.; Hashemi, M. M.; Bratcher, M. S. J. Am. Chem. Soc. 1992, 114, 1920-1. (d) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, Victoria, British Columbia, July, 1992, Abstract No. 64. (e) Cheng, P.-C. M. S. Thesis, University of Nevada, Reno, 1992. (f) Scott, L. T. International Symposium on Synthetic and Mechanistic Hydrocarbon Chemistry, Fukuoka, Japan, December 6-9, 1993, Abstract No. 7-A. (g) Cheng, P.-C. Ph.D. Dissertation, Boston College, 1996.
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49. The work of Hopf et al. on the isomerization of simple hexa-1,3-dien-5-ynes to benzenes may be relevant here: (a) Hopf, H.; Musso, H. Angew. Chem. 1969, 81, 680 (see also: Angew. Chem., Int. Ed. Engl. 1969, 8, 680). (b) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765-79. (c) Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U.; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1238 (see also: Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190). (d) Nuchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann./Recl. 1997, 1505-1515. (e) Personal communication.
50. The work of Hopf et al. on the isomerization of simple hexa-1,3-dien-5-ynes to benzenes may be relevant here: (a) Hopf, H.; Musso, H. Angew. Chem. 1969, 81, 680 (see also: Angew. Chem., Int. Ed. Engl. 1969, 8, 680). (b) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765-79. (c) Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U.; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1238 (see also: Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190). (d) Nuchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann./Recl. 1997, 1505-1515. (e) Personal communication.
51. The work of Hopf et al. on the isomerization of simple hexa-1,3-dien-5-ynes to benzenes may be relevant here: (a) Hopf, H.; Musso, H. Angew. Chem. 1969, 81, 680 (see also: Angew. Chem., Int. Ed. Engl. 1969, 8, 680). (b) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765-79. (c) Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U.; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1238 (see also: Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190). (d) Nuchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann./Recl. 1997, 1505-1515. (e) Personal communication.
52. The work of Hopf et al. on the isomerization of simple hexa-1,3-dien-5-ynes to benzenes may be relevant here: (a) Hopf, H.; Musso, H. Angew. Chem. 1969, 81, 680 (see also: Angew. Chem., Int. Ed. Engl. 1969, 8, 680). (b) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765-79. (c) Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U.; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1238 (see also: Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190). (d) Nuchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann./Recl. 1997, 1505-1515. (e) Personal communication.
53. The work of Hopf et al. on the isomerization of simple hexa-1,3-dien-5-ynes to benzenes may be relevant here: (a) Hopf, H.; Musso, H. Angew. Chem. 1969, 81, 680 (see also: Angew. Chem., Int. Ed. Engl. 1969, 8, 680). (b) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765-79. (c) Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U.; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1238 (see also: Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190). (d) Nuchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann./Recl. 1997, 1505-1515. (e) Personal communication.
54. The work of Hopf et al. on the isomerization of simple hexa-1,3-dien-5-ynes to benzenes may be relevant here: (a) Hopf, H.; Musso, H. Angew. Chem. 1969, 81, 680 (see also: Angew. Chem., Int. Ed. Engl. 1969, 8, 680). (b) Roth, W. R.; Hopf, H.; Horn, C. Chem. Ber. 1994, 127, 1765-79. (c) Hopf, H.; Berger, H.; Zimmermann, G.; Nuchter, U.; Jones, P. G.; Dix, I. Angew. Chem. 1997, 109, 1236-1238 (see also: Angew. Chem., Int. Ed. Engl. 1997, 36, 1187-1190). (d) Nuchter, U.; Zimmermann, G.; Francke, V.; Hopf, H. Liebigs Ann./Recl. 1997, 1505-1515. (e) Personal communication.
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60. 30c are also obtained. We thank Dorin Preda for tracking down and identifying these side products by comparisons with authentic samples.
61. We have used 1-chlorovinyl groups as latent ethynyl groups for the synthesis of a wide range of polycyclic aromatic hydrocarbons by flash pyrolytic methods. See, for example: (a) Necula, A.; Scott, L. T. Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June 19-22, 1994, Abstract No. 60. (b) Necula, A.; Scott, L. T. Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 114. (c) Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386-8. (d) Necula, A. Ph.D. Dissertation, Boston College, 1996. (e) Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877-1880.
62. We have used 1-chlorovinyl groups as latent ethynyl groups for the synthesis of a wide range of polycyclic aromatic hydrocarbons by flash pyrolytic methods. See, for example: (a) Necula, A.; Scott, L. T. Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June 19-22, 1994, Abstract No. 60. (b) Necula, A.; Scott, L. T. Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 114. (c) Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386-8. (d) Necula, A. Ph.D. Dissertation, Boston College, 1996. (e) Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877-1880.
63. We have used 1-chlorovinyl groups as latent ethynyl groups for the synthesis of a wide range of polycyclic aromatic hydrocarbons by flash pyrolytic methods. See, for example: (a) Necula, A.; Scott, L. T. Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June 19-22, 1994, Abstract No. 60. (b) Necula, A.; Scott, L. T. Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 114. (c) Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386-8. (d) Necula, A. Ph.D. Dissertation, Boston College, 1996. (e) Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877-1880.
64. We have used 1-chlorovinyl groups as latent ethynyl groups for the synthesis of a wide range of polycyclic aromatic hydrocarbons by flash pyrolytic methods. See, for example: (a) Necula, A.; Scott, L. T. Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June 19-22, 1994, Abstract No. 60. (b) Necula, A.; Scott, L. T. Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 114. (c) Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386-8. (d) Necula, A. Ph.D. Dissertation, Boston College, 1996. (e) Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877-1880.
65. We have used 1-chlorovinyl groups as latent ethynyl groups for the synthesis of a wide range of polycyclic aromatic hydrocarbons by flash pyrolytic methods. See, for example: (a) Necula, A.; Scott, L. T. Northeast Regional Meeting of the American Chemical Society, Burlington, VT, June 19-22, 1994, Abstract No. 60. (b) Necula, A.; Scott, L. T. Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 114. (c) Scott, L. T.; Necula, A. J. Org. Chem. 1996, 61, 386-8. (d) Necula, A. Ph.D. Dissertation, Boston College, 1996. (e) Scott, L. T.; Necula, A. Tetrahedron Lett. 1997, 38, 1877-1880.
66. 1d-g See also: (a) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S.; Corpuz, E. 12th IUPAC Conference on Physical Organic Chemistry; Padova, Italy, August 28-September 2, 1994, Abstract No. 34. (b) Cheng, P.-C.; Scott, L. T. National Meeting of the American Chemical Society; Washington, DC, August 21-26, 1994, organic division Abstract No. 87. (c) Cheng, P.-C.; Scott, L. T., Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 8.
67. 1d-g See also: (a) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S.; Corpuz, E. 12th IUPAC Conference on Physical Organic Chemistry; Padova, Italy, August 28-September 2, 1994, Abstract No. 34. (b) Cheng, P.-C.; Scott, L. T. National Meeting of the American Chemical Society; Washington, DC, August 21-26, 1994, organic division Abstract No. 87. (c) Cheng, P.-C.; Scott, L. T., Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 8.
68. 1d-g See also: (a) Scott, L. T.; Cheng, P.-C.; Bratcher, M. S.; Corpuz, E. 12th IUPAC Conference on Physical Organic Chemistry; Padova, Italy, August 28-September 2, 1994, Abstract No. 34. (b) Cheng, P.-C.; Scott, L. T. National Meeting of the American Chemical Society; Washington, DC, August 21-26, 1994, organic division Abstract No. 87. (c) Cheng, P.-C.; Scott, L. T., Eighth International Symposium on Novel Aromatic Compounds; Braunschweig, Germany, July 31-August 4, 1995, Abstract No. 8.
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82. (b) Crowley, C.; Taylor, R.; Kroto, H. W.; Walton, D. R. M.; Cheng, P.-C.; Scott, L. T. Synth. Met. 1996, 77, 17-22.
83. (a) Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-11.
84. (b) Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339-43.
85. Rabideau, P. W.; Abdourazak, A. H.; Folsom, H. E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891-2.
86. Hagen, S.; Bratcher, M. S.; Erickson, M. S.; Zimmermann, G.; Scott, L. T. Angew. Chem. 1997, 109, 407-409.
87. (See also Angew. Chem., Int. Ed. Engl. 1997, 36, 406-408.)
88. (a) Sarobe, M.; Zwikker, J. W.; Snoeijer, J. D.; Wiersum, U. E.; Jenneskens, L. W. J. Chem. Soc., Chem. Commun. 1994, 89-90.
89. (b) Sarobe, M.; Flink, S.; Jenneskens, L. W.; van Poecke, B. L. A.; Zwikker, J. W. J. Chem. Soc., Chem. Commun. 1995, 2415-16.
90. (c) Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Slagt, M. Q.; Zwikker, J. W. Tetrahedron Lett. 1995, 36, 8489-92.
91. (d) Sarobe, M.; Snoeijer, J. D.; Jenneskens, L. W.; Zwikker, J. W.; Wesseling, J. Tetrahedron Lett. 1995, 36, 9565-6.
92. (e) Jenneskens, L. W.; Sarobe, M.; Zwikker, J. W. Pure Appl. Chem. 1996, 68, 219-24.
93. See for example: Scott, L. T. Pure Appl. Chem. 1996, 68, 291-300.
94. Alternative methods for introduction of diethynylfluoranthene 3 into the pyrolysis tube met with only marginal success. A 4% yield of corannulene was obtained with use of the solution spray method of Rubin et al.: Rubin, Y.; Lin, S. S.; Knobler, C. B.; Anthony, J.; Boldi, A. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 6943-6949. A 17% yield of corannulene was obtained with use of the frozen matrix/flash sublimation method of Magrath and Fowler: Magrath, J.; Fowler, F. W. Tetrahedron Lett. 1988, 29, 2174-7.
95. Alternative methods for introduction of diethynylfluoranthene 3 into the pyrolysis tube met with only marginal success. A 4% yield of corannulene was obtained with use of the solution spray method of Rubin et al.: Rubin, Y.; Lin, S. S.; Knobler, C. B.; Anthony, J.; Boldi, A. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 6943-6949. A 17% yield of corannulene was obtained with use of the frozen matrix/flash sublimation method of Magrath and Fowler: Magrath, J.; Fowler, F. W. Tetrahedron Lett. 1988, 29, 2174-7.