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2
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0001028441
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Sapse A.-M., and Schleyer P.v.R. (Eds), Wiley-Interscience, New York, NY
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Maercker A. In: Sapse A.-M., and Schleyer P.v.R. (Eds). Lithium Chemistry: A Theoretical and Experimental Overview (1995), Wiley-Interscience, New York, NY 477-577
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, pp. 477-577
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Maercker, A.1
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3
-
-
84985502385
-
-
For a study on the formation of a radical-anion intermediate from arylcyclopropanes in the presence of sodium-potassium in THF, see:
-
For a study on the formation of a radical-anion intermediate from arylcyclopropanes in the presence of sodium-potassium in THF, see:. Boche G., and Wintermayr H. Angew. Chem., Int. Ed. Engl. 20 (1981) 874-875
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Angew. Chem., Int. Ed. Engl.
, vol.20
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Boche, G.1
Wintermayr, H.2
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5
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34247262467
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For reviews, see:
-
-
-
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8
-
-
0034904455
-
-
Yus M. Synlett (2001) 1197-1205
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(2001)
Synlett
, pp. 1197-1205
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Yus, M.1
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11
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33748199260
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Rappoport Z., and Marek I. (Eds), J. Wiley & Sons, Chichester, UK Part 2, Chapter 11
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Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 1 (2004), J. Wiley & Sons, Chichester, UK Part 2, Chapter 11
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(2004)
The Chemistry of Organolithium Compounds
, vol.1
-
-
Yus, M.1
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12
-
-
34247247073
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-
For mechanistic studies, see:
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-
-
-
18
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34247224179
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-
For a polymer supported arene-catalysed version of this reaction, see:
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-
-
-
24
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34247181567
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-
For recent reviews on polylithio intermediates, see:
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-
-
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27
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34247233662
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For a general overview, see also Ref. 2.
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-
-
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28
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2542447275
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-
The excess of lithium powder is necessary when the scale of the reaction is only 1 mmol in order to avoid the loss of the metal, which is floating on the reaction mixture and on the wall of the flask. Actually, for reactions performed at 5-10 mmol scale, a 1/2.5 substrate/lithium powder ratio is enough to be used in the arene-catalysed lithiation:
-
The excess of lithium powder is necessary when the scale of the reaction is only 1 mmol in order to avoid the loss of the metal, which is floating on the reaction mixture and on the wall of the flask. Actually, for reactions performed at 5-10 mmol scale, a 1/2.5 substrate/lithium powder ratio is enough to be used in the arene-catalysed lithiation:. Yus M., Moreno B., and Foubelo F. Synthesis (2004) 1115-1118
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(2004)
Synthesis
, pp. 1115-1118
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Yus, M.1
Moreno, B.2
Foubelo, F.3
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29
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34247185718
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For a general account on structure, reactivity and selectivity of allylic organoalkali reagents, see:
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-
-
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30
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34247263139
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Schlosser M. (Ed), J. Wiley & Sons, Chichester, UK Chapters 1.2 and 1.3
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Schlosser M. In: Schlosser M. (Ed). Organometallics in Synthesis. A Manual (1994), J. Wiley & Sons, Chichester, UK Chapters 1.2 and 1.3
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(1994)
Organometallics in Synthesis. A Manual
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Schlosser, M.1
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31
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34247272875
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For some reviews on transition-metal-catalysed allylic substitution, see:
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-
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34
-
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34247197553
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-
note
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The main by-product characterised by tandem GC-MS was in all cases propylbenzene, resulting from a reduction of the 'reduced' product propen-1-ylbenzene (11 with X=H, coming from a γ-proton abstraction by the allylic intermediate 5) by dissolving metals, probably in the work-up (addition of water in the presence of an excess of lithium powder).
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-
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35
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0041878778
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For a review on the addition of allylic organometallic reagents to carbonyl compounds, see:
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For a review on the addition of allylic organometallic reagents to carbonyl compounds, see:. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2793
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(2003)
Chem. Rev.
, vol.103
, pp. 2763-2793
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-
Denmark, S.E.1
Fu, J.2
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36
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34247225393
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Similar results have been obtained in our group for other allyllithium derivatives generated by different ways and chlorosilanes or carbonyl compounds as electrophiles:
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-
-
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37
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0033520272
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Alonso E., Guijarro D., Martínez P., Ramón D.J., and Yus M. Tetrahedron 55 (1999) 11027-11038
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(1999)
Tetrahedron
, vol.55
, pp. 11027-11038
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-
Alonso, E.1
Guijarro, D.2
Martínez, P.3
Ramón, D.J.4
Yus, M.5
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39
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34247210603
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See, for example:
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-
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40
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30844447201
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Azzena U., Dettori F., Sforazzini G., Yus M., and Foubelo F. Tetrahedron 62 (2006) 1557-1563
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(2006)
Tetrahedron
, vol.62
, pp. 1557-1563
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-
Azzena, U.1
Dettori, F.2
Sforazzini, G.3
Yus, M.4
Foubelo, F.5
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41
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33646944179
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Yang A., Butela H., Deng K., Doubleday D., and Cohen T. Tetrahedron 62 (2006) 6526-6535
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(2006)
Tetrahedron
, vol.62
, pp. 6526-6535
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Yang, A.1
Butela, H.2
Deng, K.3
Doubleday, D.4
Cohen, T.5
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42
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0037430606
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-
This compound was prepared by a modification of the procedure described in the literature ( )
-
This compound was prepared by a modification of the procedure described in the literature (. Huang J.-H., Lee T.-Y., Swenson D.C., and Messerle L. Inorg. Chim. Acta 345 (2003) 209-215 )
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(2003)
Inorg. Chim. Acta
, vol.345
, pp. 209-215
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Huang, J.-H.1
Lee, T.-Y.2
Swenson, D.C.3
Messerle, L.4
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43
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0010783715
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through the corresponding 1,1-dibromo-2,2-diphenylcyclopropane ( ) and by a final bromine-lithium exchange (see Ref. 4)
-
through the corresponding 1,1-dibromo-2,2-diphenylcyclopropane (. Shimizu N., Watanabe K., and Tsuno Y. Chem. Lett. (1983) 1877-1878 ) and by a final bromine-lithium exchange (see Ref. 4)
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(1983)
Chem. Lett.
, pp. 1877-1878
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Shimizu, N.1
Watanabe, K.2
Tsuno, Y.3
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44
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34247187289
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It is well known that THF can suffer α-deprotonation by reacting with organolithiums. See, for instance:
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-
-
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46
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For a recent report, see also:
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48
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34247242038
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An experiment proving this fact was performed as follows: after lithiation of 1,1-diphenylcyclopropane (7) and reaction with acetone, as it was described above (Table 2, entry 5), the reaction mixture was hydrolysed with deuterium oxide and no deuterium incorporation was detected (tandem GLC-MS) for both products 13e and 14e, so the capture of a proton took place before the final hydrolysis.
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51
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0012852372
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Shiragami H., Kawamoto T., Imi K., Matsubara S., Utimoto K., and Nozaki H. Tetrahedron 44 (1988) 4009-4022
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(1988)
Tetrahedron
, vol.44
, pp. 4009-4022
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Shiragami, H.1
Kawamoto, T.2
Imi, K.3
Matsubara, S.4
Utimoto, K.5
Nozaki, H.6
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59
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Chem. Abstr. 102 (1985) 45518
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Chem. Abstr.
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Chem. Abstr. 88 (1978) 136220
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Chem. Abstr.
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Acta Pharm. Suec.
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Chem. Abstr. 83 (1975) 157705
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(1975)
Chem. Abstr.
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