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70350000197
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Zonta et al. suggest the term Miyazaki-Newman-Kwart rearrangement.
-
Zonta et al. suggest the term Miyazaki-Newman-Kwart rearrangement.
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12
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17144432232
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For recent examples, see: a) A. Gallardo-Godoy, A. Fierro, T. H. McLean, M. Castillo, B. K. Casseis, M. Reyes-Parada, D. E. Nichols, J. Med. Chem. 2005, 48, 2407;
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45
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40849106264
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2NC(S)Cl is an inexpensive reagent that is available in bulk, November
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2NC(S)Cl is an inexpensive reagent that is available in bulk, see: a) D. Kusch, Spec. Chem. 2003, November, 41;
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Kusch, D.1
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33646489712
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0002079323
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The NKR has been subject to detailed mechanistic studies, most of which support reaction proceeding through A, see ref. [3b] and: a
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The NKR has been subject to detailed mechanistic studies, most of which support reaction proceeding through A, see ref. [3b] and: a) K. Miyazaki, Tetrahedron Lett. 1968, 9, 2793;
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54
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67650526327
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Cross-coupling of Ar-X with RSH has been developed extensively
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a) Cross-coupling of Ar-X with RSH has been developed extensively, see: E. Alvaro, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 7858, and references therein;
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Alvaro, E.1
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55
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0037154722
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Pd'-catalyzed allylic thiocarbamate rearrangements
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b) Pd'-catalyzed allylic thiocarbamate rearrangements: H.-J. Gais, A. Böhme, J. Org. Chem. 2002, 67, 1153;
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Gais, H.-J.1
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45849105618
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Pd'-catalyzed
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c) Pd'-catalyzed see: L. E. Overman, S. W Roberts, H. F. Sneddon, Org. Lett. 2008, 10, 1485, and references therein;
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Overman, L.E.1
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57
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84962368247
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benzylic thiocarbamates
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d) benzylic thiocarbamates: M. Alajarin, M. Martin-Luna, M.-M. Ortin, R Sanchez-Andrada, A. Vidal, Tetrahedron 2009, 65, 2579.
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Alajarin, M.1
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Sanchez-Andrada, R.4
Vidal, A.5
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58
-
-
70349993186
-
-
3 reduces the rearrangement temperature of dimethyl-0-(3-pyridyl)thiocarbamate from 250°C to 190°C, see ref.[3b];
-
3 reduces the rearrangement temperature of dimethyl-0-(3-pyridyl)thiocarbamate from 250°C to 190°C, see ref.[3b];
-
-
-
-
59
-
-
84890633748
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(Ed.: U. Lindstrom), Blackwell, Oxford
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b) see also: S. Narayan, V. V. Folkin, K. B. Sharpless in Organic Reactions in Water: Principles, Strategies and Applications (Ed.: U. Lindstrom), Blackwell, Oxford, 2007, pp. 350-365.
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Organic Reactions in Water: Principles, Strategies and Applications
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Narayan, S.1
Folkin, V.V.2
Sharpless, K.B.3
-
60
-
-
70349977413
-
-
2] (cod = cyclooctadiene)) or 100 mol% MgBr2, in refluxing toluene induced complete rearrangement of o-, m- andp-la. Substrates lb, Ic, 1g and 1h failed to rearrange under these conditions.
-
2] (cod = cyclooctadiene)) or 100 mol% MgBr2, in refluxing toluene induced complete rearrangement of o-, m- andp-la. Substrates lb, Ic, 1g and 1h failed to rearrange under these conditions.
-
-
-
-
61
-
-
84977418780
-
-
W. L. Driessen, L. M. Van Geldrop, W. L. Groeneveld, Reel. Trav. Chim. Pays-Bas 1970, 89, 1271.
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Driessen, W.L.1
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-
62
-
-
70349993187
-
-
2-1a] rearranged without cross-over.
-
2-1a] rearranged without cross-over.
-
-
-
-
63
-
-
70349900133
-
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For recent examples and leading references, see: a) L. Ackermann, A. Althammer, S. Fenner, Angew. Chem. 2009, 121, 207;
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Ackermann, L.1
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40949154756
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b) R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754;
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Munday, R.H.1
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67
-
-
70349978587
-
-
See Supporting Information for full details.
-
See Supporting Information for full details.
-
-
-
-
68
-
-
70349994396
-
-
3P ligand.
-
3P ligand.
-
-
-
-
69
-
-
70349983608
-
-
3P ligand, would minimise cross-over.
-
3P ligand, would minimise cross-over.
-
-
-
-
70
-
-
51049108168
-
-
Z. Li, Y Fu, Q.-X. Guo, L. Liu, Organometallics 2008, 27, 4043.
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Li, Z.1
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72
-
-
70349977410
-
-
-1 for step VI. The key change is thus the oxidative addition step (II), consistent with lower reactivity displayed by less electronwithdrawing substituents (Table 1).
-
-1 for step VI. The key change is thus the oxidative addition step (II), consistent with lower reactivity displayed by less electronwithdrawing substituents (Table 1).
-
-
-
-
73
-
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33751385897
-
-
The hindered N,N-dimethylthiocarbamates derived from 2,2'dihydroxy-1,1'- binaphthalene and hydroxy cyclophane (ref. [17]) have, so far, failed to undergo catalyzed rearrangement. However, it is anticipated that more efficient catalysts will be developed in due course
-
The hindered N,N-dimethylthiocarbamates derived from 2,2'dihydroxy-1,1'- binaphthalene (D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem. 1993, 58, 1748) and hydroxy cyclophane (ref. [17]) have, so far, failed to undergo catalyzed rearrangement. However, it is anticipated that more efficient catalysts will be developed in due course.
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Fabbri, D.1
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|