Regiospecific synthesis of 2,3-bisnaphthopyranyl quinones related to conocurvone. Effect of substituents on palladium-catalyzed cross-coupling of organostannanes to naphthopyranyl hydroxyquinone triflates

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 8034-8040

  Stagliano, Kenneth W ^a   Malinakova, Helena C ^a  

^a Illinois Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTIN COMPOUND; PALLADIUM; QUINONE DERIVATIVE;

ARTICLE; CATALYSIS; DECOMPOSITION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032697599     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990785v     Document Type: Article

References (49)

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2. Stagliano, K. W.; Malinakova, H. C. Tetrahedron Lett. 1997, 38(38), 6617-6620.
3. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
4. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
5. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
6. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
7. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
8. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
9. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
10. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
11. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
12. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
13. Both haloquinones and stannylquinones have been employed in palladium-catalyzed cross-coupling reactions, see: (a) Haloquinones: Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56(23), 6488-6491. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34(29), 4713-4716. Fukuyama, Y.; Kiriyama, Y.; Kodama, M. Tetrahedron Lett. 1993, 34(47), 7637-7638. Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016. Rama Devi, A.; Iyengar, D. S.; Pardhasaradhi, M. Tetrahedron 1994, 50(8), 2543-2550. Echavarren, A. M.; Tamayo, N.; Cárdenas, D. J. J. Org. Chem. 1994, 59, 9(20), 6075-6083. Gothelf, K. V.; Torssell, K. B. G. Acta Chem. Scand. 1994, 48, 61-67. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37(41), 7445-7448. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37(49), 8953-8956. Yoshida, S.; Kubo, H.; Saika, T.; Katsumura, S. Chem. Lett. 1996, 139-140. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62(21), 7072-7073.
14. (b) Stannylquinones: Liebeskind, L. S.; Riesinger, S. W. J. Org. Chem. 1993, 58(2), 408-413 and references therein. Kelly, T. R.; Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V. J. Org. Chem. 1998, 63(4), 1090-1097.
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30. The effect of the nature of the alkyl groups on the stannane, the solvent and the added LiCl on aryl vs alkyl transfer in Stille coupling reactions has been described; see: Farina, V,; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58(20), 5434-5444, and references therein.
31. 4, mediated hydroxylation; see: Echavarren, A. M.; Tamayo, N.; Cardenas, D. J. J. Org. Chem. 1994, 59(20), 6075-6083.
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33. 3As ligand, see: Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113(25), 9585-9595.
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37. Intramolecular migration of a trifluoromethanesulfonyl group in calixarene systems was reported to proceed only in the presence of a palladium catalyst, LiCl, and at least a catalytic amount of vinyl-tributyl stannane. See: Echavarren, A. M.; Gonzalez, J. J.; Nieto, P. M.; Prados, P.; de Mendoza, J. J. Org. Chem. 1995, 60(23), 7419-7423.
38. For an example of decreased reactivity toward ipso-substitution of methoxide due to the presence of an aryl ring on the quinone core, see: Liebeskind, L. S.; Yu, M. S.; Yu, R. H.; Wang, J.; Hagen, K. S. J. Am. Chem. Soc. 1993, 115(20), 9048-9055.
39. Differences in reactivity between hindered and unhindered substrates used in palladium mediated synthesis of hindered biaryls related to the michellamines have been observed: Hoye, T. R.; Chen, M. J. Org. Chem. 1996, 61(22), 7940-7942.
40. Buchman, O.; Grosjean, M.; Nasielski, J. Bull. Soc. Chim. Belg. 1962, 71, 467-472.
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42. 2 afforded the hydroxyquinone resulting from triflate decomposition as the major product accompanied by 11% of the diarylquinone. Unpublished results.
43. Presumably, increased steric hindrance about the cross-coupling site and/or chelation of the MOM group in 9 to palladium could be responsible for the observed phenomenon. Chelation of an electron-donor group to palladium is known to give rise to stable cyclometalated complexes; see: Bruce, M. I. Angew. Chem., Int. Ed. Engl. 1997, 16, 73-86.
44. The reduction of electron-deficient quinone electrophiles during the Stille coupling leading to recovery of the uncoupled hydroquinone has been observed; see: Chan, K. S.; Mak, C. C. Tetrahedron 1994, 50(7), 2003-2016.
45. Loss of trifluoromethanesulfinate ion from aryl triflates has been observed; see: Creary, X.; Benage, B.; Hilton, K. J. Org. Chem. 1983, 48(17), 2887-2891.
46. For a discussion of substituent effects on reversible half-wave potentials of quinone/hydroquinone couples, see: Chambers, J. Q. In The Chemistry of the Functional Groups. The Chemistry of the Quinonoid Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1974; Part 2, Chapter 14.
47. The use of remote substituents to control the regiochemistry of the Diels-Alder reaction in naphthoquinone systems has been summarized: Naruta Y.; Maruyama, K. In The Chemistry of the Quinonoid Compounds; Patai, S., Rappoport, Z., Ed.; John Wiley & Sons: New York, 1988; Vol. 2, pp 292-303.
48. 13C NMR spectra. The spectra are still useful for identification of the structure of these compounds. Chemical shifts of the satellite peaks arising from the hindered rotation are indicated in parentheses following the parent signals.
49. Hewgill, R. F.; Mullings, L. R. Aust. J. Chem. 1975, 28(2), 355-367.