5396
M. Kar et al. / Bioorg. Med. Chem. Lett. 15 (2005) 5392–5396
G. O.; Ashcroft, J.; Ellestad, G. A. J. Am. Chem. Soc.
References and notes
1989, 111, 6888; (g) Nicolaou, K. C.; Dai, W.-M. J. Am.
Chem. Soc. 1992, 114, 8908.
8. Konig, B.; Hollnagel, H.; Ahrens, B.; Jones, P. G. Angew
Chem. Int. Ed. Engl. 1995, 34, 2538.
9. Shinkai, S.; Minami, T.; Kasano, Y.; Manabe, O. J. Am.
Chem. Soc. 1983, 105, 1851; Vogtle, F. In Supramolecular
Chemistry An Introduction; Wiley: Chichester, UK, 1989,
Chapter 7.
10. Delaire, J. A.; Nakatani, K. Chem. Rev. 2000, 100, 1817.
11. Ichimura, K. Chem. Rev. 2000, 100, 1847.
12. Aemissegger, A.; Krautler, V.; van Gunstaren, W. F.;
Hilvert, D. J. Am. Chem. Soc. 2005, 127, 2929.
13. (a) Bhattacharyya, S.; Pink, M.; Baik, Mu. H.; Zaleski, J.
M. Angew Chemie Int. Ed. 2005, 44, 592; (b) Basak, A.;
Bag, S. S.; Majumder, P. A.; Das, A. K.; Bertolasi, V. J.
Org. Chem. 2004, 69, 6927; (c) Koenig, B.; Leue, S.; Horn,
C.; Caudan, A.; Desvergne, J.-P.; Bouas-Laurent, H.
Liebigs Annalen 1996, 1231; (d) Hopf, H.; Jones, P. G.;
Bubenitschek, P.; Werner, C. Angew Chemie Int. Ed. 1995,
34, 2367; (e) Koenig, B.; Fricke, T.; Dix, I.; Jones, P. G. J.
Chem. Res. Synop. 1997, 68; (f) Koenig, B.; Pitsch, W.;
Thondorf, I. J. Org. Chem. 1996, 61, 4258.
1. (a) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene
Chemistry; Stang, P. J., Diederich, F., Eds.; VCH:
Weinheim, 1995, p 203; (b) Maier, M. E. Synletters
1995, 13; (c) Dai, W. M.; Nicolaou, K. C. Angew Chem.
Int. Ed. Engl. 1991, 30, 1387; (d) Lhermite, H.; Grierson,
D. Contemp. Org. Synth. 1996, 3, 93; (e) Grissom, J. W.;
Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahe-
dron 1996, 52, 6453.
2. (a) Nicolaou, K. C.; Sorensen, E. J.; Discordia, R.;
Hwang, C.-K.; Minto, R. E.; Bharucha, K. N.; Bergman,
R. G. Angew Chem. Int. Ed. Engl. 1994, 33, 1044; (b)
Banfi, L.; Guanti, G. Angew Chem. Int. Ed. Engl. 1995, 34,
2393; (c) Basak, A.; Khamrai, U. K.; Mallick, U. K. J.
Chem. Soc. Chem. Commun. 1996, 749.
3. (a) Magnus, P.; Fairhurst, R. A. J. Chem. Soc. Chem.
Commun. 1994, 1541; (b) Snyder, J. P. J. Am. Chem. Soc.
1990, 112, 5367; (c) Magnus, P.; Carter, P.; Elliott, J.;
Lewis, R.; Harling, J.; Patterna, T.; Butta, W. E.; Fortt, S.
J. Am. Chem. Soc. 1992, 114, 2544.
4. (a) Basak, A.; Mandal, S.; Bag, S. S. Chem. Rev. 2003, 103,
4077; (b) Rawat, D. S.; Benites, P. J.; Incarvito, C. D.;
Rheingold, A. L.; Zaleski, J. M. Inorg. Chem. 2001, 40,
1846; (c) Coalter, N.; Concolino, T. E.; Streib, W. E.;
Hughes, C. G.; Rheingold, A. L.; Zaleski, J. M. J. Am.
Chem. Soc. 2000, 122, 3112; (d) Benites, P. B.; Rawat, D.
S.; Zaleski, J. M. J. Am. Chem. Soc. 2000, 122, 7208; (e)
Konig, B.; Rutters, H. Tetrahedron Lett. 1994, 35, 350; (f)
Warner, B. P.; Miller, S. P.; Broee, R. D.; Buchwald, S. L.
Science 1995, 269, 814.
5. (a) David, W. M.; Kerwin, S. M. J. Am. Chem. Soc. 1997,
119, 1464; (b) Kraka, E.; Cremer, D. J. Am. Chem. Soc.
2000, 122, 8245; (c) Hoffner, J.; Schottelius, J. M.;
Feichtinger, D.; Chen, P. J. Am. Chem. Soc. 1998, 120,
376; Alabugin, I. V.; Manoharan, M.; Kovalenko, S. V.
Org. Lett. 2002, 4, 1119; Alabugin, I. V.; Manoharan, M.
J. Phys. Chem. A 2003, 107, 3363; Basak, A.; Kar, M.;
Mandal, S. Bioorg. Med. Chem. Lett. 2005, 15, 2061.
6. Basak, A.; Mandal, S.; Das, A. K.; Bertolasi, V. Bioorg.
Med. Chem. Lett. 2002, 12, 873; Schmittel, M.; Kiau, S.
Chem. Lett. 1995, 953.
7. (a) Basak, A.; Roy, S. K.; Mandal, S. Angew Chem. Int.
Ed. 2005; (b) Lee, M. D.; Dunne, T. S.; Siegel, M. M.;
Chang, C. C.; Morton, G. O.; Borders, D. B. J. Am.
Chem. Soc. 1987, 109, 3464; (c) Golik, J.; Clardy, J.;
Dubay, G.; Groenwold, G.; Kawaguchi, H.; Saitoh, K.;
Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3462; (d) De
Voss, J. J.; Townsend, C. A.; Ding, W.-D.; Morton, G. O.;
Ellestad, G. A.; Zein, N.; Tabor, A. B.; Schreiber, S. L. J.
Am. Chem. Soc. 1990, 112, 9669; (e) De Voss, J. J.;
Hangeland, J. J.; Townsend, C. A. J. Am. Chem. Soc.
1990, 112, 4554; (f) Zein, N.; McGahren, W. J.; Morton,
14. Nuss, J. M.; Murphy, M. M. Tetrahedron Lett. 1994, 35,
37.
15. (a) Sonogashira, K.; Tohoda, Y.; Hagihara, N. Tetrahe-
dron Lett. 1975, 16, 4467; (b) Takahashi, S.; Kuroyama,
Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627; (c)
Crout, D. H. G.; Gaudet, V. S. B.; Laumen, K.; Schneider,
M. J. Chem. Soc. Chem. Commun. 1986, 808; Fukuyama,
T.; Cheung, M.; Jow, C.-K.; Hidai, Y.; Kan, T. Tetrahe-
dron Lett. 1997, 38, 5831.
16. Spartan MM2 software presented to us on a limited day
trial basis.
17. Konig, B.; Schofield, E.; Bubenitschek, P.; Jones, P. G. J.
Org. Chem. 1994, 59, 7142.
18. This was in conformity to our theoretical predictions. It
may be pointed out that the solution-phase kinetics for
BC widely differs from the solid state reactivity. The
rate of isomerization from Z to E is too fast in
solution which prevented us from comparing the
solution -phase reactivity of the two isomers. In the
solid phase the rate of such isomerization was much
slower, which allowed us to measure the onset temper-
ature for BC for pure Z isomers by increasing the rate
of heat supply. DSC measurement to follow the
isomerization of
Z
to E-isomer of 2,20-diallyloxy
azobenzene expectedly showed a small exothermic peak
starting at a high temperature of 143 ꢁC. Thus, the
exothermic peak associated with high heat change
(possible for BC followed by polymerization) as seen
in the DSC for the cis-azo compounds can be predicted
to be due to BC.