Page 11 of 12
Journal of the American Chemical Society
7
.
Fielder, S.; Rowan, D. D.; Sherburn, M. S. Angew. Chem., Int. Ed.
2000, 39, 4331.
Payne, A. D.; Bojase, G.; Paddon-Row, M. N.; Sherburn, M. S.
Angew. Chem., Int. Ed. 2009, 48, 4836.
Hata, T.; Masai, H.; Kitagawa, H.; Shimizu, M.; Hiyama, T. Tetrahedron
2002, 58, 6381.
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
5
5
5
5
6
8
.
26.
(a) Shimizu, M.; Kurahashi, T.; Hiyama, T. Synlett 2001, SI,
1006. (b) Shimizu, M.; Kurahashi, T.; Shimono, K.; Tanaka, K.; Nagao, I.;
Kiyomoto, S.-I.; Hiyama, T. Chem. Asian J. 2007, 2, 1400.
9
.
Bailey, W. J.; Nielsen, N. A. J. Org. Chem. 1962, 27, 3088.
1
0.
(a) Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506.
27.
(a) Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P.
(
b) Grimme, W.; Rother, H.- J. Angew. Chem., Int. Ed. 1973, 12, 505. (c)
Tetrahedron 2006, 62, 7521. (b) Barluenga, J.; Moriel, P.; Aznar, F.; Valdés,
C. Adv. Synth. Catal. 2006, 348, 347. (c) Bojase, G.; Payne, A. D.; Willis, A.
C.; Sherburn, M. S. Angew. Chem., Int. Ed. 2008, 47, 910. (d) Kohnen, A.
L.; Danheiser, R. L. Org. Synth. 2007, 84, 77. (e) Kottirsch, G.; Szeimies, G.
Chem. Ber. 1990, 123, 1495.
Bee, L. K.; Everett, J. W.; Garratt, P. J. Tetrahedron 1977, 33, 2143. (d)
Roth, W. R.; Scholz, B. P.; Breuckmann, R.; Jelich, K.; Lennartz, H.-W.
Chem. Ber. 1982, 115, 1934. (e) Payne, A. D.; Willis, A. C.; Sherburn, M. S.
J. Am. Chem. Soc. 2005, 127, 12188.
1
1.
D. W. H.; Henry, W. J.; Gosney, I. J. Org. Chem. 1997, 62, 2767.
2. (a) Hopf, H.; Maas, G. Angew. Chem., Int. Ed. 1992, 31, 931. (b)
Maas, G.; Hopf, H. Synthesis and Transformation of Radialenes
Online];PATAI’s Chemistry of Functional Groups, John Wiley & Sons,
Brain, P. T.; Smart, B. A.; Robertson, H. E.; Davis, M. J.; Rankin,
28.
Shimizu, M.; Tanaka, K.; Kurahashi, T.; Shimono, K.; Hiyama,
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
T. Chem. Lett. 2004, 33, 1066.
29.
Koizumi, T.-A.; Ishii, D.; Nakagawa, M.; Mashiko, Y.; Shimizu, N. Bull.
Chem. Soc. Jpn. 2006, 79, 498. (b) Hopf, H.; Theurig, M. Angew. Chem., Int.
Ed. 1994, 33, 1099.
1
(a) Yamamoto, T.; Yasuda, T.; Kobayashi, K.; Yamaguchi, I.;
[
Ltd., 2009; pp 1–51. (c) Hopf, H. Classics in Hydrocarbon Chemistry: Syn-
theses, Concepts, Perspectives; Wiley-VCH:Weinheim, 2000; pp 290–300.
1
P. A.; Sanders, E. B.; Peterson, L. I.; Griffin, G. W. J. Am. Chem. Soc. 1967,
9, 6318. (c) Kozhushkov, S. I.; Leonov, A.; de Meijere, A. Synthesis 2003,
56. (d) Wright, C.; Holmes, J.; Nibler, J. W.; Hedberg, K.; White, J. D.;
Hedberg, L.; Weber, A.; Blake, T. A. J. Phys. Chem. A 2013, 117, 4035.
1
15.
30.
For a summary of reaction conditions examined, see Supporting
3.
(a) Dorko, E. A. J. Am. Chem. Soc. 1965, 87, 5518. (b) Waitkus,
Information.
31.
(a) Rahimi, A.; Schmidt, A. Synthesis 2010, 2010, 2621. (b)
8
9
Chelucci, G.; Capitta, F.; Baldino, S. Tetrahedron 2008, 64, 10250. (c)
Chelucci, G.; Capitta, F.; Baldino, S.; Pinna, G. A. Tetrahedron Lett. 2007,
48, 6514. (d) Jacobsen, M. F.; Moses, J. E.; Adlington, R. M.; Baldwin, J. E.
Org. Lett. 2005, 7, 641. (e) Jacobsen, M. F.; Moses, J. E.; Adlington, R. M.;
Baldwin, J. E. Tetrahedron 2006, 62, 1675. (f) Yan, H.; Lu, L.; Sun, P.; Zhu,
Y.; Yang, H.; Liu, D.; Rong, G.; Mao, J. RSC Adv. 2013, 3, 377. (g) Liu, J.;
Dai, F.; Yang, Z.; Wang, S.; Xie, K.; Wang, A.; Chen, X.; Tan, Z. Tetrahe-
dron Lett. 2012, 53, 5678. (h) Shen, W.; Wang, L. J. Org. Chem. 1999, 64,
8873. (i) Zapata, A. J.; Ruíz, J. J. Organomet. Chem. 1994, 479, C6.
4.
Trabert, L.; Hopf, H. Liebigs Ann. Chem. 1980, 1980, 1786.
Mackay, E. G.; Newton, C. G.; Toombs-Ruane, H.; Lindeboom,
E. J.; Fallon, T.; Willis, A. C.; Paddon-Row, M. N.; Sherburn, M. S.
5]Radialene. J. Am. Chem. Soc. [Online early access]. DOI:
[
1
0.1021/jacs.5b07445.
6. (a) Harruff, L. G.; Brown, M.; Boekelheide, V. J. Am. Chem. Soc.
978, 100, 2893. (b) Höpfner, T.; Jones, P. G.; Ahrens, B.; Dix, I.; Ernst,
1
1
32.
Sondheimer, F.; Ben-Efraim, D. A.; Wolovsky, R. J. Am. Chem.
L.; Hopf, H. Eur. J. Org. Chem. 2003, 2003, 2596.
7. (a) Woerly, E. M.; Roy, J.; Burke, M. D. Nat. Chem. 2014, 6,
Soc. 1961, 83, 1675.
33.
Chemistry, 3rd ed.; McGraw-Hill:London, 1980; pp 6–11.
34.
and [7]dendralene reported in our 2009 study (see reference 8) are slightly
different to those reported here.
35.
mono-adducts is ca. 85:15 (terminal:internal mono-adduct). This ratio is
reversed in [4]dendralene. A similar analysis of the bis-adducts shows a ca.
75% preference for the terminal/terminal regioisomer. The termi-
nal/internal regioisomer dominates with [4]dendralene (65% selectivity).
1
Williams, D. H.; Fleming, I. Spectroscopic Methods in Organic
484. (b) Hopf, H. Classics in Hydrocarbon Chemistry: Syntheses, Concepts,
Perspectives; Wiley-VCH:Weinheim, 2000; pp 103–112.
The magnitudes of extinction coefficients for [5]dendralene
1
8.
gets, Strategies, Methods, 1st ed.; VCH:Weinheim, 1996.
9. (a) Hückel, E. Z. Phys. 1931, 70, 204. (b) Hückel, E. Z. Phys.
931, 72, 310. (c) Hückel, E. Z. Phys. 1932, 76, 628.
Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis: Tar-
1
1
By H NMR spectroscopic analysis, the product ratio of the
1
2
0.
Spitler, E. L.; Johnson, C. A.; Haley, M. M. Chem. Rev. 2006,
1
06, 5344.
21.
(a) Boese, R.; Weiss, H.-C.; Bläser, D. Angew. Chem., Int. Ed.
1999, 38, 988. (b) Thalladi, V. R.; Boese, R.; Weiss, H.-C. J. Am. Chem. Soc.
000, 122, 1186. (c) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc.
000, 122, 9227. (d) van Langevelde, A.; Peschar, R.; Schenk, H. Chem.
36.
(a) Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. J. Chem.
2
2
Phys. 2007, 126, 084108. (b) Curtiss, L. A.; Redfern, P. C.; Raghavachari,
K. J. Chem. Phys. 2007, 127, 124105.
37.
J. Phys. Chem. 1995, 99, 578. (b) Pratt, L. R.; Hsu, C. S.; Chandler, D. J.
Chem. Phys. 1978, 68, 4202.
38.
P.; Lehrich, F.; Nielsen, C. J.; Powell, D. L.; Trætteberg, M. Acta Chem.
Scand. Ser. A 1988, 42, 634.
Mater. 2001, 13, 1089. (e) White, N. A. S.; Ellis, H. A.; Nelson, P. N.; Ma-
ragh, P. T. J. Chem. Thermodyn. 2011, 43, 584. (f) Ramin, L.; Jabbarzadeh,
A. Langmuir 2011, 27, 9748. (g) Nelson, P. N.; Ellis, H. A.; Taylor, R. A. J.
Mol. Struct. 2011, 986, 10. (h) Nelson, P. N.; Ellis, H. A. Dalton Trans.
2012, 41, 2632. (i) Bhattacharya, S.; Saraswatula, V. G.; Saha, B. K. Cryst.
Growth Des. 2013, 13, 3651. (j) de la Rama, L. P.; Hu, L.; Ye, Z.; Efremov,
M. Y.; Allen, L. H. J. Am. Chem. Soc. 2013, 135, 14286. (k) Nelson, P. N.;
Ellis, H. A. J. Mol. Struct. 2014, 1075, 299.
(a) Herrebout,W. A.; van der Veken, B. J.; Wang, A.; Durig, J. R.
Almenningen, A.; Gatial, A.; Grace, D. S. B.; Hopf, H.; Klaeboe,
39.
Palmer, M. H.; Blair-Fish, J. A.; Sherwood, P. J. Mol. Struct.
1997, 412, 1.
40.
2
2.
Improved syntheses of [7]dendralene and [8]dendralene in-
Lodewyk, M. W.; Soldi, C.; Jones, P. B.; Olmstead, M. M.; Rita,
volving lynchpin approaches are described in the Supporting Information.
2
023.
24.
J.; Shaw, J. T.; Tantillo, D. J. J. Am. Chem. Soc. 2012, 134, 18550.
41.
42.
832.
3.
Jacobsen, E. N.; Bergman, R. G. J. Am. Chem. Soc. 1985, 107,
(a) Reich, H. J.; Yelm, K. E.; Reich, I. L. J. Org. Chem. 1984, 49,
Chai, J.-D.; Head-Gordon, M. J. Chem. Phys. 2008, 128, 084106.
Paddon-Row, M. N.; Sherburn, M. S. Chem. Commun. 2012, 48,
2
3438. (b) Wille, F.; Dirr, K.; Kerber, H. Justus Liebigs Ann. Chem. 1955,
91, 177. (c) Sajadi, S. A. A.; Pruhan, G. H.; Mostaghim, R. Nashrieh Shimi
va Mohandesi Shimi Iran 2003, 22, 39.
5. (a) Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu,
5
2
M.; Hiyama, T. Angew. Chem., Int. Ed. 2001, 40, 790. (b) Kurahashi, T.;
SYNOPSIS TOC
ACS Paragon Plus Environment