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and Ref therein
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33
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0001449812
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CH2-H ∼ 0 Hz) between the oxirane β-hydrogen and the carbon of the methylene group (or of the methyl group) of the substituent on the α-carbon, as reported: Kingsbury, C. A.; Durham, D. L.; Hutton, R. J. Org. Chem. 1978, 43, 4696-4700. The configuration to 2h/2i and 5e was assigned either by analogy to similar trisubstituted aryl methyl oxazolinyloxiranes as reported in ref 16 or by analogy to 5d, respectively. The configuration to the inseparable diastereomers 2j could not be assigned.
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Kingsbury, C.A.1
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Abbotto, A.1
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(a) Florio, S.; Capriati, V.; Luisi, R. Tetrahedron Lett. 1996, 37, 4781-4784.
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(b) Capriati, V.; Florio, S.; Luisi, R.; Russo, V.; Salomone, A. Tetrahedron Lett. 2000, 41, 8835-8838.
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0037039907
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(d) Lithiated 2-chloromethyl-2-oxazoline is an extremely reactive intermediate for undergoing smooth homocoupling reaction to give transbis(oxazolinyl)ethene and trans-1,2,3-tris(oxazolinyl)cyclopropane, as reported: Capriati, V.; Florio, S.; Luisi, R.; Rocchetti, M. T. J. Org. Chem. 2002, 67, 759-763.
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Abbotto, A.; Capriati, V.; Degennaro, L.; Florio, S.; Luisi, R.; Pierrot, M.; Salomone, A. J. Org. Chem. 2001, 66, 3049-3058.
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41
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(b) Mordini, A.; Ben Rayana, E.; Margot, C.; Schlosser, M. Tetrahedron 1990, 46, 2401-2410.
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(c) Margot, C.; Rizzolio, M.; Schlosser, M. Tetrahedron 1990, 46, 2411-2424.
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0037040653
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and ref therein
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(d) Bertilsson, S. K.; Södergren, M. J.; Andersson, P. G. J. Org. Chem. 2002, 67, 1567-1573 and ref therein.
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Bertilsson, S.K.1
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45
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0003409730
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Wiley: New York; Chapter 4
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3J(CN,H) coupling constants between the iminic carbon and the olefinic proton. In the case of the E isomers (having a cis-type arrangement between the above groups) couplings have been found to be always smaller (7.5-8.5 Hz) than those of the Z ones (10.6-11.5 Hz) as reported for similar π-bonded systems: Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: New York, 1988; Chapter 4, pp 526-543.
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Kalinowski, H.-O.1
Berger, S.2
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46
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0034701307
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LDA is recognized to exist as a disolvated dimer in ethereal solvents (Sun, X.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 2452-2458), while s-BuLi complexed by TMEDA is usually monomeric going towards an endothermic disproportionation from a 1:1 complex to a 1:2 complex according to the temperature (Catala, J. M.; Clouet, G.; Brossas, J. J. Organomet. Chem. 1981, 219, 139-143).
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J. Am. Chem. Soc.
, vol.122
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Sun, X.1
Collum, D.B.2
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47
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2242495636
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LDA is recognized to exist as a disolvated dimer in ethereal solvents (Sun, X.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 2452-2458), while s-BuLi complexed by TMEDA is usually monomeric going towards an endothermic disproportionation from a 1:1 complex to a 1:2 complex according to the temperature (Catala, J. M.; Clouet, G.; Brossas, J. J. Organomet. Chem. 1981, 219, 139-143).
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(1981)
J. Organomet. Chem.
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Catala, J.M.1
Clouet, G.2
Brossas, J.3
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48
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2242449972
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note
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The possibility that the lower stereoselection of reactions promoted by LDA could be attributed to an isomerization reaction of Z isomers into E isomers promoted by the formed diisopropylamine can be ruled out. Indeed, Z-8a, Z-8b, and Z-8d do not isomerize to the corresponding E isomers when treated with diisopropylamine and E-8d does not isomerize to Z-8d.
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49
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2242421202
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note
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All efforts made in order to separate diastereomers 5d and 5e failed so far.
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