Abstract
Photoirradiation of 1-cyano-2-(2,2-dicyano-5-phenylpentyn-4-yl)naphthalene and its analogues promotes sequential intramolecular [2π + 2π] photocycloaddition and cyclobutene ring opening to form benzocyclooctatetraenes, which are then transformed to benzotriquinanes in good yields via a photochemical transannular cyclization process.
Similar content being viewed by others
Notes and references
J. J. McCullough, Chem. Rev. 1987, 87, 811–860.
J. Cornelisse, Chem. Rev. 1993, 93, 615–669.
K. Mizuno, H. Maeda, A. Sugimoto and K. Chiyonobu, in Molecular and Supramolecular Photochemistry, ed. V. Ramamurthy and K. S. Schanze, Marcel Dekker, New York, 2001, vol.8, pp. 127–241.
N. Hoffmann, in Molecular and Supramolecular Photochemistry, ed. A. G. Griesbeck and J. Mattay, Marcel Dekker, New York, 2005, vol.12, pp. 529–552.
M. Oelgemöller and W. H. Kramer, J. Photochem. Photobiol., C 2010, 11, 210–244.
P. A. Wender and J. J. Howbert, J. Am. Chem. Soc. 1981, 103, 688–690.
P. A. Wender, R. Ternansky, M. deLong, S. Singh, A. Olivero and K. Rice, Pure Appl. Chem. 1990, 62, 1597–1602.
K. Mizuno, H. Maeda, Y. Inoue, A. Sugimoto, L. P. Vo and R. A. Caldwell, Tetrahedron Lett. 2000, 41, 4913–4916.
H. Maeda, S. Waseda and K. Mizuno, Chem. Lett. 2000 1238–1239.
H. Maeda, A. Sugimoto and K. Mizuno, Org. Lett. 2000, 2, 3305–3308.
A. Yokoyama and K. Mizuno, Org. Lett. 2000, 2, 3457–3459.
J. J. McCullough, W. K. MacInnis, C. J. L. Lock and R. Faggiani, J. Am. Chem. Soc. 1980, 102, 7780–7782.
J. J. McCullough, W. K. MacInnis, C. J. L. Lock and R. Faggiani, J. Am. Chem. Soc. 1982, 104, 4644–4658.
K. Mizuno, S. Konishi, T. Tanaka and H. Inoue, Tetrahedron Lett. 1996, 37, 7775–7778.
K. Mizuno, S. Konishi, Y. Yoshimi and A. Sugimoto, Chem. Commun. 1998 1659–1660.
Y. Yoshimi, S. Konishi, H. Maeda and K. Mizuno, Tetrahedron Lett. 2001, 42, 3475–3477.
Y. Yoshimi, S. Konishi, H. Maeda and K. Mizuno, Synthesis 2001 1197–1202.
H. Maeda, H. Mukae and K. Mizuno, Chem. Lett. 2005 66–67.
D. Bryce-Smith, A. Gilbert and B. H. Orger, J. Chem. Soc., Chem. Commun. 1966 512–514.
Y. Inoue, K. Nishida, K. Ishibe, T. Hakushi and N. J. Turro, Chem. Lett. 1982 471–474.
N. Zupancic and B. Sket, J. Chem. Soc., Perkin Trans. 1 1992 179–180.
D. Döpp and H. R. Memarian, Chem. Ber. 1990, 123, 315–319.
G. Sugowdz, P. J. Collin and W. H. F. Sasse, Tetrahedron Lett. 1969, 10, 3843–3846.
W. H. F. Sasse, Aust. J. Chem. 1969, 22, 1257–1264.
W. H. F. Sasse, P. J. Collin, D. B. Robert and G. Sugowdz, Aust. J. Chem. 1971, 24, 2151–2171.
P. J. Collin and W. H. F. Sasse, Aust. J. Chem. 1971, 24, 2325–2338.
T. Teitei, P. J. Collin and W. H. F. Sasse, Aust. J. Chem. 1972, 25, 171–182.
T. Teitei and D. Wells, Tetrahedron Lett. 1975, 16, 2299–2302.
W. Lippke, W. Ferree Jr. and H. Morrison, J. Am. Chem. Soc. 1974, 96, 2134–2137.
M. C. Pirrung, J. Org. Chem. 1987, 52, 1635–1637.
Q.-J. Liu, Y.-M. Shen, H.-Y. An, G. Grampp, S. Landgraf and J.-H. Xu, Tetrahedron 2006, 62, 1131–1138.
, 3455 and 4272; Q. Liu, Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, 63, 2901
Q. Liu, D. Shi and J. Xu, J. Chem. Crystallgr. 2003, 33, 263–267.
Q. Liu, R. Qu and J. Xu, Acta Crystallogr., Sect. E: Struct. Rep. Online 2003, 59, 1246–1248.
H. Mukae, H. Maeda and K. Mizuno, Angew. Chem., Int. Ed. 2006, 45, 6558–6560.
C. O. Bender, D. L. Bengtson, D. Dolman and S. F. O’Shea, Can. J. Chem. 1986, 64, 237–245.
C. O. Bender, D. L. Bengtson, D. Dolman and R. T. McKay, Can. J. Chem. 1994, 72, 1556–1564.
C. O. Bender, D. Dolman, J. C. Foesier, S. L. Lawson and K. E. Preuss, Can. J. Chem. 2003, 81, 37–44.
C. O. Bender, I. M. Cassis, D. Dolman, L. D. Heerze and F. L. Schultz, Can. J. Chem. 1984, 62, 2769–2776.
C. O. Bender, D. Dolman and N. Tu, J. Org. Chem. 1991, 56, 5015–5020.
T. Hudlicky and J. W. Reed, Angew. Chem., Int. Ed. 2010, 49, 4864–4876.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to the memory of Professor Nicholas J. Turro (Columbia University).
Rights and permissions
About this article
Cite this article
Mizuno, K., Negoro, N., Nagayama, Y. et al. Formation of a new benzotriquinane skeleton via intramolecular photocycloaddition reactions of a phenylethynes moiety to a 1-cyanonaphthalene ring system. Photochem Photobiol Sci 13, 145–148 (2014). https://doi.org/10.1039/c3pp50243k
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c3pp50243k