Organic Letters
Letter
(3) For thermal conditions, see (a) Diels, O.; Alder, K. Justus Liebigs
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(4) Becker, H.-D. Chem. Rev. 1993, 93, 145−172 and references
therein..
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8889−8894. (b) Fujiwara, Y.; Ozawa, R.; Onuma, D.; Suzuki, K.;
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1
(10) The E/Z configuration of 8 was assigned by the H NMR
chemical shift of the vinyl hydrogen that has cis relationship to a
sulfinyl group appears at a lower field compared to that of the trans
counterpart. For details, see ref 9.
(11) The rotamer ratio is estimated by 1H NMR. The major isomer
shows a pair of doublets (δ 7.93 and 7.95, J = 3.3 Hz), assigned for
protons at C(9) and C(10) on the anthracene core, which indicated
its unsymmetrical structure. Minor isomers independently show a
singlet at δ 8.20 and 8.38 assignable for protons at the C(9) and
C(10) positions, which proved their symmetrical structures, but in no
particular order. Interconversion of these isomers was not observed by
NOE experiments on the NMR time scale (600 MHz).
(12) (a) Fukuzumi, S.; Kochi, J. K. Tetrahedron 1982, 38, 1035−
1049. (b) Hirsch, A. K. H.; Reutenauer, P.; Le Moignan, M.; Ulrich,
S.; Boul, P. J.; Harrowfield, J. M.; Jarowski, P. D.; Lehn, J.-M. Chem. -
Eur. J. 2014, 20, 1073−1080. (c) Kiselev, V. D.; Kornilov, D. A.;
Anikin, O. V.; Shulyatiev, A. A.; Konovalov, A. I. J. Solution Chem.
2019, 48, 31−44.
(13) The prolonged reaction time (5 h, 110 °C) allowed further
atropisomerization, giving 10a as a single isomer, albeit in a low yield
(37%).
(14) The reaction conditions were optimized by our previous study;
see ref 6a.
1
(15) The E/Z configuration of 11 was assigned by the H NMR
chemical shift of the vinyl hydrogen and the 13C NMR chemical shifts
of the allylic carbon, which appear at lower fields compared to their cis
counterpart. For details, see ref 6a.
(16) Crabtree, R. Acc. Chem. Res. 1979, 12, 331−337.
(18) For a basis of this strategy, see Huang, Z.-A.; Chen, C.; Yang,
X.-D.; Fan, X.-B.; Zhou, W.; Tung, C.-H.; Wu, L.-Z.; Cong, H. J. Am.
Chem. Soc. 2016, 138, 11144−11147.
(19) Miyake, H.; Tsumura, T.; Sasaki, M. Tetrahedron Lett. 2004, 45,
7213−7215.
(20) Only two of three possible isomers were detected. The
stereostructures were not determined.
(21) (a) Bouas-Laurent, H.; Castellan, A.; Desvergne, J.-P.;
Lapouyade, R. Chem. Soc. Rev. 2001, 30, 248−263. (b) Takaguchi,
Y.; Tajima, T.; Ohta, K.; Motoyoshiya, J.; Aoyama, H. Chem. Lett.
2000, 29, 1388−1389.
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Org. Lett. XXXX, XXX, XXX−XXX