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[1a] Propargylic epoxides are useful precursors of homopropargylic alcohols, see: N. Bernard, F. Chemla, N. Normant, Tetrahedron Lett. 1998, 39, 6715-6718. -
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Bernard, N.1
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[1b] D. Grandjean, P. Pale, J. Chuche, Tetrahedron 1993, 49, 5225-5236. -
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[1c] D. Grandjean, J. Chuche, P. Pale, Bull. Soc. Chim. Belg. 1992, 101, 415. -
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[2b] A. Alexakis, I. Marek, P. Mangeney, J. F. Normant, Tetrahedron 1991, 47, 1677-1696.
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Alexakis, A.1
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G.-A. Cao, Z.-X. Wang, J. Tu, Y. Shi, Tetrahedron Lett. 1998, 39, 4425-4428 and refs. therein.
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Cao, G.-A.1
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Shi, Y.4
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D. Bernard, A. Doutheau, J. Gore, J. Moulinoux, V. Quemener, J. Chantepie, G. Quash, Tetrahedron 1989, 45, 1429-1439.
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Bernard, D.1
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Moulinoux, J.4
Quemener, V.5
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D. Grandjean, P. Pale, J. Chuche, Tetrahedron Lett. 1992, 33, 5355-5358.
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D. Grandjean, P. Pale, J. Chuche, Tetrahedron Asymmetry 1993, 4, 1991-1994.
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[7a] F. Chemla, N. Bernard, J. F. Normant, Tetrahedron Lett. 1999, 40, 75-78. -
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[7b] F. Chemla, V. Hebbe, J. F. Normant, Tetrahedron Lett. 1999, 40, 8093-8096.
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[8b] U. H. Brinker, Methoden der Organischen Chemie (Hauben Weyl), Georg Thieme Verlag, Stuttgart, New York, 1989, Vol. E19b/Teil 1, pp. 337-663. -
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Brinker, U.H.1
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18
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0007004011
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note
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The homocoupling reaction between cinnamyl chloride (α-attack) and its lithiated derivative (γ-attack) proceeded regioselectively so that the geometry about the C-C double bond remained unchanged in 2 and consequently in the chlorohydrin 3 and the epoxide 4 as well.
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19
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0000970350
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The chemical shift found for the olefinic proton of 5b (δ = 6.83) is in excellent agreement with the value estimated (δ = 6.81) for a Z geometry utilizing Simon's additive shielding parameters for the prediction of NMR shifts, as reported by U. E. Matter, C. Pascual, E. Pretsch, A. Pross, W. Simon, S. Sternhell, Tetrahedron 1969, 25, 691-697.
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(1969)
Tetrahedron
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Matter, U.E.1
Pascual, C.2
Pretsch, E.3
Pross, A.4
Simon, W.5
Sternhell, S.6
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20
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0025980278
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[12a] S. Florio, G. Ingrosso, L. Ronzini, E. Epifani, Tetrahedron 1991, 47, 3365-3374. -
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(1991)
Tetrahedron
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Florio, S.1
Ingrosso, G.2
Ronzini, L.3
Epifani, E.4
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21
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0001449812
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[12b] C. A. Kingsbury, D. L. Durham, R. Hutton, J. Org. Chem. 1978, 43, 4696-4700. -
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(1978)
J. Org. Chem.
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Kingsbury, C.A.1
Durham, D.L.2
Hutton, R.3
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22
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0001045032
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[12c] S. Florio, V. Capriati, V. Russo, Gazz. Chim. Ital. 1997, 127, 587-595.
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(1997)
Gazz. Chim. Ital.
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Florio, S.1
Capriati, V.2
Russo, V.3
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23
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0000110756
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The chloro substituent has been chosen as the "large" group on the basis of frontier molecular orbital arguments that the ligand with the lowest-lying σ* orbital, rather than the sterically most demanding group, is perpendicular to the carbonyl plane and anti to the attacking nucleophile (E. P. Lodge, C. H. Heathcock, J. Am. Chem. Soc. 1987, 109, 3353-3361).
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(1987)
J. Am. Chem. Soc.
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Lodge, E.P.1
Heathcock, C.H.2
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24
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20544433165
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On the other hand, the chlorine atom has almost the same van der Waals volume as the methyl group (A. Bondi, J. Phys. Chem. 1964, 68, 441-451).
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(1964)
J. Phys. Chem.
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Bondi, A.1
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0032558617
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S. Florio, L. Troisi, V. Capriati, Tetrahedron Lett. 1998, 39, 7951-7954.
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Florio, S.1
Troisi, L.2
Capriati, V.3
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26
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0007050698
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note
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The stereochemistries of epoxide 4e and aziridine 8c were confirmed on the basis of their NOESY spectra.
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28
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33947290993
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α-Halo imines can easily be synthesized from α-halo ketones and primary amines as reported: [17a] K. Taguchi, F. H. Westheimer, J. Org. Chem. 1971, 36, 1570-1572. -
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(1971)
J. Org. Chem.
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Taguchi, K.1
Westheimer, F.H.2
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0026568580
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[17b] N. De Kimpe, W. De Cock, C. Stevens, Tetrahedron 1992, 48, 2739-2760.
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(1992)
Tetrahedron
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De Kimpe, N.1
De Cock, W.2
Stevens, C.3
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30
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0007004013
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note
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Chloro amines 7a-c, which are the probable intermediates en route to the formation of aziridines 8a-c, could not be isolated.
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