Delicate Equilibrium between Tetracene and Cyclobutene
[3] a) K. Saxena, D. S. Mehta, V. K. Rai, R. Srivastava, G. Chau-
han, M. N. Kamalasanan, V. K. Jain, Phys. Status Solidi A
2009, 206, 1660; b) H.-H. Huang, S.-Y. Chu, P.-C. Kao, Y.-C.
Chena, Thin Solid Films 2008, 516, 5669; c) D.-H. Lee, J. S.
Choi, H. Chae, C.-H. Chung, S. M. Cho, Curr. Appl. Phys.
2009, 9, 161; d) Z. Wang, Y. Lou, S. Naka, H. Okada, J. Lumin.
2010, 130, 1198; e) B. Ding, W. Zhu, X. Jiang, Z. Zhang, Solid
State Commun. 2008, 148, 226; f) A. M. C. Ng, A. B. Djurisˇic,
W.-K. Chan, J.-M. Nunzi, Chem. Phys. Lett. 2009, 474, 141.
[4] a) V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L.
Willett, T. Someya, M. E. Gershenson, J. A. Rogers, Science
2004, 303, 1644; b) J. Takeya, M. Yamagishi, Y. Tominari, R.
Hirahara, Y. Nakazawa, T. Nishikawa, T. Kawase, T. Shimoda,
S. Ogawa, Appl. Phys. Lett. 2007, 90, 102120; c) D. Braga, G.
Horowitz, Adv. Mater. 2009, 21, 1473; d) A. Molinari, I. Gu-
tiérrez, I. N. Hulea, S. Russo, A. F. Morpurgo, Appl. Phys.
Lett. 2007, 90, 212103; e) V. Podzorov, E. Menard, A. Borissov,
V. Kiryukhin, J. A. Rogers, M. E. Gershenson, Phys. Rev. Lett.
2004, 93, 086602; f) J. E. Anthony, Chem. Rev. 2006, 106, 5028;
g) D. A. F. da Silva, E.-G. Kim, J.-L. Brédas, Adv. Mater. 2005,
17, 1072.
[13]
[14]
[15]
O. D. Jurchescu, A. Meetsma, T. T. M. Palstra, Acta Crys-
tallogr., Sect. B 2006, 62, 330.
a) J. Rigaudy, P. Capdevielle, Tetrahedron 1977, 33, 767; b) T. L.
Jacobs, D. M. Fenton, J. Org. Chem. 1965, 30, 1808.
a) A. J. Brattesani, E. Maverick, O. J. Muscio Jr., T. L. Jacobs,
J. Org. Chem. 1992, 57, 7346; b) E. V. Dehmlow, G. C. Ezi-
mora, Tetrahedron Lett. 1972, 13, 1265; c) E. V. Dehmlow, An-
gew. Chem. Int. Ed. Engl. 1972, 11, 322; d) B. Alcaide, P. Al-
mendros, C. Aragoncillo, Chem. Soc. Rev. 2010, 39, 783.
C. Dufraisse, J. Mathieu, J. J. Valls, C. R. Acad. Sci. 1958, 246,
661.
M. Christl, M. Rudolph, E.-M. Peters, K. Peters, H. G.
von Schnering, Angew. Chem. Int. Ed. Engl. 1995, 34, 2730.
M. D. Schiavelli, S. C. Hixon, H. W. Moran, C. J. Boswell, J.
Am. Chem. Soc. 1971, 93, 6989.
J. D. Roberts, C. M. Sharts, Org. React. 1962, 12, 1.
a) J. J. Gajewski, C. N. Shih, J. Am. Chem. Soc. 1967, 89, 4532;
b) J. J. Gajewski, C. N. Shih, J. Am. Chem. Soc. 1969, 91, 5900;
c) J. J. Gajewski, C. N. Shih, J. Org. Chem. 1972, 37, 64; d) J. J.
Gajewski, C. N. Shih, J. Am. Chem. Soc. 1972, 94, 1675.
[16]
[17]
[18]
[19]
[20]
[5] a) R. Zeis, C. Besnard, T. Siegrist, C. Schlockerman, Z. Chi,
C. Kloc, Chem. Mater. 2006, 18, 244; b) C. Kloc, K. J. Tan,
M. L. Toh, K. K. Zhang, Y. P. Xu, Appl. Phys. A: Mater. Sci.
Process 2009, 95, 219; c) T. Hosokawa, H. Nakano, K. Takami,
K. Kobiro, A. Shiga, Tetrahedron Lett. 2003, 44, 1175.
[6] a) A. S. Paraskar, A. R. Reddy, A. Patra, Y. H. Wijsboom, O.
Gidron, L. J. W. Shimon, G. Leitus, M. Bendikov, Chem. Eur.
J. 2008, 14, 10639; b) E. V. Banide, B. C. Molloy, Y. Ortin, H.
Müller-Bunz, M. J. McGlinchey, Eur. J. Org. Chem. 2007, 2611;
c) L. E. Harrington, J. F. Britten, M. J. McGlinchey, Tetrahe-
dron Lett. 2003, 44, 8057; d) L. E. Harrington, J. F. Britten,
M. J. McGlinchey, Org. Lett. 2004, 6, 787; e) E. V. Banide, Y.
Ortin, C. M. Seward, L. E. Harrington, H. Müller-Bunz, M. J.
McGlinchey, Chem. Eur. J. 2006, 12, 3275; f) J. A. Dodge, J. D.
Bain, A. R. Chamberlin, J. Org. Chem. 1990, 55, 4190; g) Z.
Chen, P. Müller, T. M. Swager, Org. Lett. 2006, 8, 273; h) Y.-
C. Lin, C.-H. Lin, Org. Lett. 2007, 9, 205; i) E. Yagodkin, C. J.
Douglas, Tetrahedron Lett. 2010, 51, 3037; j) Y. Hou, X. Chi,
X. Wan, Y. Chen, J. Mol. Struct. 2008, 889, 265.
[7] K. Hess, W. Weltzien, Ber. Dtsch. Chem. Ges. 1921, 54, 2511;
more recently the propargyl alcohols were synthesized in com-
parable chemical yields by addition of lithium or potassium
acetylides to the corresponding benzophenones, see: S. G. R.
Guinot, J. D. Hepworth, M. Wainwright, Dyes Pigm. 2000, 47,
129.
[8] a) E. J. Corey, P. L. Fuchs, Tetrahedron Lett. 1972, 13, 3769; b)
J. P. Beny, S. N. Dhawan, J. Kagan, S. Sundlass, J. Org. Chem.
1982, 47, 2201.
[21]
[22]
a) P. Oulié, L. Altes, S. Milosevic, R. Bouteille, H. Müller-
Bunz, M. J. McGlinchey, Organometallics 2010, 29, 676; b)
E. V. Banide, P. Oulié, H. Müller-Bunz, M. J. McGlinchey, Or-
ganometallics 2008, 27, 5657.
a) P. Oulié, L. Altes, S. Milosevic, R. Bouteille, H. Müller-
Bunz, M. J. McGlinchey, Organometallics 2010, 29, 676; b) F.
Toda, Eur. J. Org. Chem. 2000, 1377; c) F. Toda, H. Ishihara,
K. Akagi, Tetrahedron Lett. 1969, 10, 2531; d) W. D. Hunts-
man, H. J. Wristers, J. Am. Chem. Soc. 1967, 89, 342; e) R. Pal,
R. J. Clark, M. Manoharan, I. V. Alabugin, J. Org. Chem. 2010,
75, 8689.
[23] E. V. Banide, P. Oulié, M. J. McGlinchey, Pure Appl. Chem.
2009, 81, 1.
[24] a) F. Toda, K. Tanaka, T. Tamashima, M. Kato, Angew. Chem.
Int. Ed. 1998, 37, 2724; b) G. Kaupp, J. Schmeyers, M. Kato,
K. Tanaka, F. Toda, J. Phys. Org. Chem. 2002, 15, 148.
[25] a) N. Islam, T. Ooi, T. Iwasawa, M. Nishiuchi, Y. Kawamura,
Chem. Commun. 2009, 574; b) for synthesis via copper car-
benoids, see: M. Iyoda, H. Otani, M. Oda, Y. Kai, Y. Baba, N.
Kasai, J. Am. Chem. Soc. 1986, 108, 5371; c) for synthesis via
nickel carbenoids, see: M. Iyoda, M. Sakaitani, T. Miyazaki,
M. Oda, Chem. Lett. 1984, 2005; d) M. Iyoda, A. Mizusuna,
M. Oda, Chem. Lett. 1988, 149.
[26] B. H. Bui, P. R. Schreiner, Eur. J. Org. Chem. 2006, 4187.
[27] E. V. Banide, Y. Ortin, B. Chamiot, A. Cassidy, J. Niehaus, A.
Moore, C. M. Seward, H. Müller-Bunz, M. J. McGlinchey, Or-
ganometallics 2008, 27, 4173.
[9] Compound 3a is commonly used to prepare commercial rub-
rene. The transformation of this alcohol into rubrene was ac-
complished by both methods described in this paper.
[28] F. Toda, Y. Takehira, J. Chem. Soc., Chem. Commun. 1975,
174.
[29] W. Rao, P. Wai Hong Chan, Org. Biomol. Chem. 2010, 8, 4016.
[30] A.-H. Feng, J.-Y. Chen, L.-M. Yang, G.-H. Lee, Y. Wang, T.-
Y. Luh, J. Org. Chem. 2001, 66, 7922.
[10] B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2001, 123, 8862,
and references therein.
[11] Y. Zhang, J. Wen, J. Fluorine Chem. 1990, 47, 533.
[12] J. Ye, J. Ge, X. Chen, Z. Zhao, P. Lu, Tetrahedron 2007, 63
11040; for acetylenic dimerization catalysed by cuprous salts,
see also: B. J. Dahl, N. S. Mills, Org. Lett. 2008, 10, 5605.
[31] R. S. Tranter, W. Tang, K. B. Anderson, K. Brezinsky, J. Phys.
Chem. A 2004, 108, 3406, and references cited therein.
Received: January 10, 2011
Published Online: May 12, 2011
Eur. J. Org. Chem. 2011, 4160–4169
© 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
4169