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3-complex, proceeds with inversion in the second step (1 → 4 → 5): (a) Faller, J. W.; Linebarrier, D. Organometallics 1988, 7, 1670. (b) Ward, Y. D.; Villanueva, L. A.; Allerd, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 897.
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0001606220
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2), the mechanism apparently involves the usual inversion 1 → 2 followed by thermodynamic equilibration 2 → 4: Vitagliano, A.; Åkermark, B.; Hanson, S. Organometallics 1991, 10, 2592.
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33748655215
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While this work was in progress, Bäckvall published the same transformation in the cyclohexane series (7a → 8a): Gatti, R. G. P.; Carson, A. L. E.; Bäckvall, J.-E. J. Chem. Soc., Perkin Trans. 1 1997, 577.
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For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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Brown, J.M.1
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33845374498
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For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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Crabtree, R.H.1
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For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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Burk, M.J.1
McGrath, M.P.2
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47
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37049079765
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For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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Kočovský, P.1
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48
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0000287486
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For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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Breit, B.1
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49
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0030484567
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For reviews on steering the reagent/catalyst by a neighboring group, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. (b) Brown, J. M. Angew. Chem., Int Ed. Engl. 1987, 26, 190. See also: (c) Crabtree, R. H.; Davis, M. W. J. Org. Chem. 1986. 51, 2655. (d) Burk, M. J.; McGrath, M. P.; Wheeler, R.; Crabtree, R. H. J. Am. Chem. Soc. 1988, 110, 5034. For recent examples, see, e.g.: (e) Kočovský, P. J. Chem. Soc., Perkin Trans. 1 1994, 1759 and references therein. (f) Breit, B. J. Chem. Soc., Chem. Commun. 1997, 591. (g) Breit, B. Angew. Chem., Int. Ed. 1997, 35, 2835.
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Angew. Chem., Int. Ed.
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, pp. 2835
-
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Breit, B.1
-
50
-
-
84920313108
-
-
note
-
All yields refer to "isolated" yields.
-
-
-
-
51
-
-
84920313107
-
-
note
-
The Mitsunobu reaction using the alcohol obtained on saponification of either acetate 13 or 14 failed to produce the required syn-epimer, giving mainly elimination products.
-
-
-
-
52
-
-
0000411633
-
-
Yamamoto, Y.; Yatagai, H.; Maruyama, K.; Sonoda, A.; Murahashi, S. J. Am. Chem. Soc. 1977, 99, 5652.
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Yamamoto, Y.1
Yatagai, H.2
Maruyama, K.3
Sonoda, A.4
Murahashi, S.5
-
54
-
-
84920313106
-
-
note
-
2Pd, p-benzoquinone, LiCl, and AcOLi in an AcOH-hexane mixture proved essential for the reaction to proceed with acceptable efficiency, with the formation of the products of the competing Diels-Alder addition of p-BQ to the diene 18 being substantially reduced.
-
-
-
-
55
-
-
2642648930
-
-
Thesis, Royal Institute of Technology, Stockholm
-
1H NMR, as derived from a large series of compounds, see: Nordberg, R. Thesis, Royal Institute of Technology, Stockholm, 1982. The characteristic features are as follows: chemical shifts of the corresponding allylic protons are consistently higher for the trans-series by ∼0.1 ppm and their W/2 values (width at half-height of the multiplet) are typically twice as large. Thus, (E)-1,4-diacetoxycyclohex-2-ene shows CH-OAc at δ 5.32 (m, W/2 = 11 Hz), whereas its Z-counterpart exhibits this proton at δ 5.23 (m, W/2 = 8 Hz). Analogously, the products of monosubstitution of the latter diacetates with malonate give the following values for the allylic protons: 2.98 (m) and 5.28 (m, W/2 = 16 Hz) for the E-isomer and 2.88 (m) and 5.19 (m, W/2 = 9 Hz) for the Z-isomer. The data obtained for our compounds are in line with this generalization.
-
(1982)
-
-
Nordberg, R.1
-
57
-
-
0000824652
-
-
(b) Shull, B. K.; Sakai, T.; Nichols, J. B.; Koreeda, M. J. Org. Chem. 1997, 62, 8294.
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Shull, B.K.1
Sakai, T.2
Nichols, J.B.3
Koreeda, M.4
-
58
-
-
84920313105
-
-
note
-
2 singlet at 5.00 ppm), the corresponding proton in 27a appears at 5.17 ppm as ddd (J = 3, 5.5, and 9 Hz).
-
-
-
-
59
-
-
84920313104
-
-
note
-
n at 29.3, 127.3, and 129.4 ppm.
-
-
-
-
60
-
-
84920313103
-
-
note
-
22
-
-
-
-
61
-
-
84920313102
-
-
note
-
3-complexes of Pd, see ref 23.
-
-
-
-
62
-
-
0000674932
-
-
Granberg, K. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 6858. For correction, see: J. Am. Chem. Soc. 1994, 116, 10853.
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Granberg, K.L.1
Bäckvall, J.-E.2
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63
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84920306813
-
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Granberg, K. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 6858. For correction, see: J. Am. Chem. Soc. 1994, 116, 10853.
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64
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33845378604
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(a) Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033.
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Auburn, P.R.1
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65
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33845379753
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(b) Mackenzie, P. B.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2046.
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66
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0003487210
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University Science Books: Mill Valley, CA
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The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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Collman, J.P.1
Hegedus, L.S.2
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67
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0001460764
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The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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Genêt, J.P.4
Denis, A.5
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68
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33845279769
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The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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Moreno-Mañas, M.1
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Virgili, A.3
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69
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0002320171
-
-
The "Bosnich mechanism" was actually first proposed by Collman and Hegedus: (a) Collman, J. P.; Hegedus, L. S. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; p 692. For further examples, see refs 6b, 8, 23, 26, and (b) Bäckvall, J.-E.; Vågberg, J. O.; Zercher, G.; Genêt, J. P.; Denis, A. J. Org. Chem. 1987, 52, 5430. (c) Moreno-Mañas, M.; Ribas, J.; Virgili, A. J. Org. Chem. 1988, 53, 5328. (d) Kurosawa, H.; Ogoshi, S.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Chem. Lett. 1990, 1745.
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Kurosawa, H.1
Ogoshi, S.2
Chatani, N.3
Kawasaki, Y.4
Murai, S.5
Ikeda, I.6
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70
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85005596387
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Bäckvall, J.-E.; Granberg, K. L.; Heumann, A. Isr. J. Chem. 1991, 31, 17.
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Bäckvall, J.-E.1
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Heumann, A.3
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71
-
-
84920313101
-
-
note
-
23,26 However, the reaction of 9 with malonate anion proved to be highly stereoselective (vide supra) so that this possibility can be ruled out.
-
-
-
-
72
-
-
84920313100
-
-
note
-
2CH, their steric effect on the ultimate environment of the double bond is, in fact, similar, as revealed by molecular modeling. Therefore, if only the steric effect of the N-substituent were taken into account, little difference in reactivity (i.e., in the reaction rate) would be anticipated for 9 and 10.
-
-
-
-
73
-
-
84920313099
-
-
note
-
Note that this analysis lends further credence to the rejection of a similar mechanism for the cyclic series (Scheme 7).
-
-
-
-
74
-
-
0000764255
-
-
(a) Consiglio, G.; Morandini, F.; Piccolo, O. J. Am. Chem. Soc. 1981, 103, 1846.
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(b) Consiglio, G.; Piccolo, O.; Roncetti, L.; Morandini, F. Tetrahedron 1986, 41, 2043.
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Consiglio, G.1
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(a) Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273.
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84920313098
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note
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2O at room temperature for 2 h, is capricious and the procedure shown in the Experimental Section represents the most successful batch.
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-
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80
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84920313097
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note
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2. However, in view of the stoichiometric nature of this reaction, it was only used in order to obtain an authentic sample of 49.
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81
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Bäckvall, J.-E.; Nordberg, R. E.; Zetterberg, K.; Åkermark, B. Organometallics 1983, 2, 1625.
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82
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0002954650
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Rearrangements of Carbocations
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de Mayo, P., Ed.; Academic: New York
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The maximum deviation from the perfect alignment that is tolerated, seems to be ∼30°, as derived from the investigation of Wagner-Meerwein rearrangements in a series of rigid, polycyclic skeletons: Saunders: M.; Chandrasekhar, J.; Schleyer, P. v. R. Rearrangements of Carbocations. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980: Vol. 1, pp 24-34.
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Saunders, M.1
Chandrasekhar, J.2
Schleyer, P.V.R.3
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83
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84981922386
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This scenario parallels the occurrence of both anti-and synmechanisms for the E2 elimination reactions. For leading reviews, see: (a) Sicher, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 200. (b) Sicher, J. Pure Appl. Chem. 1971, 22, 655. (c) Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453.
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Sicher, J.1
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84
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84937193511
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This scenario parallels the occurrence of both anti-and synmechanisms for the E2 elimination reactions. For leading reviews, see: (a) Sicher, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 200. (b) Sicher, J. Pure Appl. Chem. 1971, 22, 655. (c) Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453.
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Sicher, J.1
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85
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0000570356
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This scenario parallels the occurrence of both anti-and synmechanisms for the E2 elimination reactions. For leading reviews, see: (a) Sicher, J. Angew. Chem., Int. Ed. Engl. 1972, 11, 200. (b) Sicher, J. Pure Appl. Chem. 1971, 22, 655. (c) Bartsch, R. A.; Závada, J. Chem. Rev. 1980, 80, 453.
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Bartsch, R.A.1
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49149145492
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N2′), see: (b) Magid, R. M. Tetrahedron 1980, 36, 1901.
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Magid, R.M.1
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(c) Hill, R. S.; Becalska, A.; Chiem, N. Organometallics 1991, 10, 2104.
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Hill, R.S.1
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Dasse, O.A.5
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94
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0001650763
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For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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Gallina, C.1
Ciattini, P.G.2
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95
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0000749009
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For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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Goering, H.L.1
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96
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0000303655
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-
and refs given therein
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For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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Tseng, C.C.1
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97
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0003547689
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and refs given therein
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For a similar stereochemical switch in the cuprate-mediated allylic substitution, see: (a) Gallina, C.; Ciattini, P. G.; J. Am. Chem. Soc. 1979, 101, 1035. (b) Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715. (c) Tseng, C. C.; Yen, S. J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892 and refs given therein. (d) Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gómez, A. M. J. Org. Chem. 1990, 55, 2294 and refs given therein.
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Valverde, S.1
Bernabé, M.2
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Gómez, A.M.4
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99
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84920313096
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note
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43 requires the coordinating group to be located at the carbon more distant than in the δ-position.
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