Construction of a tube-like molecule via sequential cyclopropylidene dimerisation and intramolecular [π2s+π2s] cycloaddition reactions

Chemical Communications

Volumn , Issue 12, 1996, Pages 1469-1470

  Banwell, Martin G ^a   Hockless, David C R ^a   Walter, Justine M ^b  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008816427     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001469     Document Type: Article

References (24)

1. J. J. Wolff, Angew. Chem., Int. Ed. Engl., 1995, 34, 2225 and reference cited therein.
2. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
3. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
4. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
5. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
6. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
7. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
8. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
9. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
10. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
11. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
12. For an overview of cyclopropylidene dimer chemistry, see J. Backes and U. H. Brinker, Methoden der Organischen Chemie, ed. M. Regitz, Georg Thieme, Stuttgart, 1989, vol. E19b, p. 391. For specific examples, see W. R. Moore and H. R. Ward, J. Org. Chem., 1960, 25, 2073; E. T. Marquis and P. D. Gardner, J. Chem. Soc., Chem. Commun. 1966, 726; W. R. Moore and R. D. Bach, J. Am. Chem. Soc., 1972, 94, 3148; K. G. Taylor, J. Chaney and J. C. Deck, J. Am. Chem. Soc., 1976, 98, 4163; Y. Fukuda, Y. Yamamoto, K. Kimura and Y. Odaira, Tetrahedron Lett., 1979, 877; P. Warner, S. H.-C. Chang, D. R. Powell and R. A. Jacobson, Tetrahedron Lett., 1981, 22, 533; J. Arct and L. Skattebøl, Acta Chem. Scand., 1982, B36, 593; G. Pilidis, Coll. Czech. Chem. Commun. 1986, 51, 2151; L. Skattebøl, Y. Stenstrøm and M-B, Stjerna, Acta Chem. Scand., 1988, B42, 475; A. P. Molchanov, S. A. Kalyamin and R. R. Kostikov, Zh. Org. Khim. SSSR, 1992, 28, 102.
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