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1
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66449131595
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Taken in part from the Ph.D. Thesis of G. Wei, Duquesne University, 2007.
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Taken in part from the Ph.D. Thesis of G. Wei, Duquesne University, 2007.
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3
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66449101689
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North, M. Nitriles: General Methods and Aliphatic Nitriles. In ComprehensiVe Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; 3, pp 611-640.
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(b) North, M. Nitriles: General Methods and Aliphatic Nitriles. In ComprehensiVe Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 3, pp 611-640.
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5
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0002779654
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Preparation and Synthetic Applications of Cyano Compounds
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Patai, S, Ed, Wiley: New York
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(b) Fatiadi, A. J. Preparation and Synthetic Applications of Cyano Compounds. In The Chemistry of Functional Groups. Supplement C; Patai, S., Ed.: Wiley: New York, 1983; pp 1157-1190.
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Fatiadi, A.J.1
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7
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Terpenoids
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Mann, J, Davidson, R. S, Hobbs, J. B, Banthorpe, D. V, Harborne, J. B, Eds, Addison Wesley Longman Ltd, Reading, MA, Chapter 5
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Banthorpe, D. V. Terpenoids. In Natural Products: Their Chemistry and Biological Significance; Mann, J., Davidson, R. S., Hobbs, J. B., Banthorpe, D. V., Harborne, J. B., Eds.; Addison Wesley Longman Ltd.: Reading, MA, 1994; Chapter 5.
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(1994)
Natural Products: Their Chemistry and Biological Significance
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Banthorpe, D.V.1
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9
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34848916346
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For a recent example see: Fleming, F. F.; Liu, W.; Ghosh, S.; Steward, O. W. Angew. Chem., Int. Ed. 2007, 46, 7098. For a review of cyclic nitrile alkylations see: Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1.
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For a recent example see: Fleming, F. F.; Liu, W.; Ghosh, S.; Steward, O. W. Angew. Chem., Int. Ed. 2007, 46, 7098. For a review of cyclic nitrile alkylations see: Fleming, F. F.; Shook, B. C. Tetrahedron 2002, 58, 1.
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10
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66449091338
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Podlech, J
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Podlech, J.
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11
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33645385475
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Introduction of the Cyano Group by Conjugate Addition, Houben-Weyl, Murahashi, S.-i, Ed, Georg Thieme: Stuttgart, Germany
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(a) Introduction of the Cyano Group by Conjugate Addition. In Science of Synthesis (Houben-Weyl); Murahashi, S.-i., Ed.; Georg Thieme: Stuttgart, Germany, 2004; Vol. 19, pp 311-324.
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(a) Pellissier, H.; Michellys, P.-Y.; Santelli, M. Steroids 2007, 72, 297.
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Pellissier, H.1
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15
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66449095496
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For an example where NMR was unable to resolve the stereochemistry of a nitrile-bearing carbon see
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For an example where NMR was unable to resolve the stereochemistry of a nitrile-bearing carbon see: Smith, P. H.; Fine, S. M.; Del Paggio, A. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1985, C41, 581.
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Acta Crystallogr., Sect. C: Cryst. Struct. Commun
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Smith, P.H.1
Fine, S.M.2
Del Paggio, A.A.3
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16
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37049092189
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(a) Takasuka, M.; Saito, T.; Yamakawa, M. J. Chem. Soc., Perkin Trans. 2 1984, 419.
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(1984)
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Takasuka, M.1
Saito, T.2
Yamakawa, M.3
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17
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84868947106
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Nagata, W.; Yoshioka, M.; Narisada, M.; Watanabe, H. Tetrahedron Lett. 1964, 3133. No citations of these references were located using SciFinder Scholar (02/06/09). Whereas an empirical correlation exists between the band intensity and configuration, the stretching frequency, at least for cyclohexanecarbonitrile, is the same for both diastereomers: Horntvedt, H. T.; Klæboe, P. Acta Chem. Scand. 1975, 29, 528.
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(b) Nagata, W.; Yoshioka, M.; Narisada, M.; Watanabe, H. Tetrahedron Lett. 1964, 3133. No citations of these references were located using SciFinder Scholar (02/06/09). Whereas an empirical correlation exists between the band intensity and configuration, the stretching frequency, at least for cyclohexanecarbonitrile, is the same for both diastereomers: Horntvedt, H. T.; Klæboe, P. Acta Chem. Scand. 1975, 29, 528.
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18
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49149136294
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Kinetic hydrocyanation of decalones installs axial nitriles whereas both isomers can form under thermodynamic conditions: Agami, C, Fadlallah, M, Levisalles, J. Tetrahedron 1981, 37, 903
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Kinetic hydrocyanation of decalones installs axial nitriles whereas both isomers can form under thermodynamic conditions: Agami, C.; Fadlallah, M.; Levisalles, J. Tetrahedron 1981, 37, 903.
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20
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34447326159
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(a) Fleming, F. F.; Wei, G.; Zhang, Z.; Steward, O. W. J. Org. Chem. 2007, 72, 5270.
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(2007)
J. Org. Chem
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Fleming, F.F.1
Wei, G.2
Zhang, Z.3
Steward, O.W.4
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21
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33644517212
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(b) Fleming, F. F.; Zhiyu, Z.; Wei, G.; Steward, O. W. J. Org. Chem. 2006, 71, 1430.
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(2006)
J. Org. Chem
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Fleming, F.F.1
Zhiyu, Z.2
Wei, G.3
Steward, O.W.4
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22
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66449128054
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Searches conducted on December 17, 2008 using SciFinder Scholar.
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Searches conducted on December 17, 2008 using SciFinder Scholar.
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23
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66449114763
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Insufficient data prevented the analysis from being extended to 5- and 7-membered cyclic nitriles. Exploratory comparisons of the 13C NMR chemical shifts for 2-cyanopiperidines show minimal differences for the nitrile carbon in axial and equatorial diastereomers: Wolckenhauser, S. A.; Rychnovsky, S. D. Tetrahedron 2005, 61, 3371.
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Insufficient data prevented the analysis from being extended to 5- and 7-membered cyclic nitriles. Exploratory comparisons of the 13C NMR chemical shifts for 2-cyanopiperidines show minimal differences for the nitrile carbon in axial and equatorial diastereomers: Wolckenhauser, S. A.; Rychnovsky, S. D. Tetrahedron 2005, 61, 3371.
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24
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4944263814
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Heteroatom substituents on the nitrile-bearing carbon induce different anisotropy effects. From the limited available chemical shifts of cyclohexanone cyanohydrins, equatorially oriented nitriles resonate further downfield than their axial counterparts in the 13C NMR: Kobler, C.; Bohrer, A.; Effenberger, F. Tetrahedron 2004, 60, 10397.
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Heteroatom substituents on the nitrile-bearing carbon induce different anisotropy effects. From the limited available chemical shifts of cyclohexanone cyanohydrins, equatorially oriented nitriles resonate further downfield than their axial counterparts in the 13C NMR: Kobler, C.; Bohrer, A.; Effenberger, F. Tetrahedron 2004, 60, 10397.
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25
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66449121187
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Many of the configurational assignments were based on crystallographic analyses or made by chemical correlation. Configurational assignments were often evident from diagnostic coupling constants at other ring positions and in other cases were made by assuming that the small nitrile adopts the more sterically demanding axial orientation
-
Many of the configurational assignments were based on crystallographic analyses or made by chemical correlation. Configurational assignments were often evident from diagnostic coupling constants at other ring positions and in other cases were made by assuming that the small nitrile adopts the more sterically demanding axial orientation.
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26
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66449117481
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The structures, the 13C NMR shifts, and the references are collated in tables provided in the Supporting Information.
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The structures, the 13C NMR shifts, and the references are collated in tables provided in the Supporting Information.
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27
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66449110402
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Long chain nitriles resonate from d119-122 (refs 20a and 20b) while alkylsubstituted benzonitriles resonate from d117-121 (ref 20c).
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Long chain nitriles resonate from d119-122 (refs 20a and 20b) while alkylsubstituted benzonitriles resonate from d117-121 (ref 20c).
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29
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84986737496
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(b) Terent'ev, A. B.; Dostovalova, V. I.; Freidlina, R. K. Org. Magn. Reson. 1977, 9, 301.
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(c) Haupt, E. T. K.; Leibfritz, D. Spectrochim. Acta, Part A 1989, 45A, 119.
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Haupt, E.T.K.1
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31
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66449105651
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Aromatic methine signals occasionally extend into the nitrile region but are readily differentiated from the quaternary nitrile signals by DEPT NMR
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Aromatic methine signals occasionally extend into the nitrile region but are readily differentiated from the quaternary nitrile signals by DEPT NMR.
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35
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(a) Takeuchi, Y.; Fujisawa, H.; Noyori, R. Org. Lett. 2004, 6, 4607.
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0005558568
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For interaction of the carbonyl p-system with the nitrile see: (a) Agami, C.; Kazakos, A.; Levisalles, J.; Sevin, A. Tetrahedron 1980, 36, 2977.
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For interaction of the carbonyl p-system with the nitrile see: (a) Agami, C.; Kazakos, A.; Levisalles, J.; Sevin, A. Tetrahedron 1980, 36, 2977.
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57
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0018367867
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(b) Agami, C.; Fadlallah, M.; Kazakos, A.; Levisalles, J. Tetrahedron 1979, 35, 969.
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Agami, C.1
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58
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0002390099
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Cross, A. D.; Harrison, I. T. J. Am. Chem. Soc. 1963, 85, 3223. The effect of adjacent carbonyl groups is evident in nitriles i and ii where the quaternary nitriles resonate in the normal region while the tertirary nitriles resonate abnormally upfield. The assignment of the nitrile carbon resonances is made by analogy to the chemical shifts of similar -oxonitiles (ref 32a) which differs from the assignment in the original report (ref 32b).
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Cross, A. D.; Harrison, I. T. J. Am. Chem. Soc. 1963, 85, 3223. The effect of adjacent carbonyl groups is evident in nitriles i and ii where the quaternary nitriles resonate in the "normal" region while the tertirary nitriles resonate abnormally upfield. The assignment of the nitrile carbon resonances is made by analogy to the chemical shifts of similar -oxonitiles (ref 32a) which differs from the assignment in the original report (ref 32b).
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59
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0037415522
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(a) Fleming, F. F.; Shook, B. C.; Jiang, T.; Steward, O. W. Tetrahedron 2003, 59, 737.
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Tetrahedron
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Fleming, F.F.1
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Steward, O.W.4
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(b) Rissafi, B.; Rachiqi, N.; El Louzi, A.; Loupy, A.; Petit, A.; Fkih-Tétouani, S. Tetrahedron 2001, 57, 2761.
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Tetrahedron
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Rissafi, B.1
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Loupy, A.4
Petit, A.5
Fkih-Tétouani, S.6
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62
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66449104780
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The conformational mobility of the cis-decalin (8′aS)-methyl-6′-oxo-octahydro-spiro[[1,3]dioxolane-2, 2′-naphthalene, 4′aR)-carbonitrile (ref 34a) averages the anisotropy induced by the adjacent bonds: Johan Winne, personal communication
-
The conformational mobility of the cis-decalin (8′aS)-methyl-6′-oxo-octahydro-spiro[[1,3]dioxolane-2, 2′-naphthalene]-(4′aR)-carbonitrile (ref 34a) averages the anisotropy induced by the adjacent bonds: Johan Winne, personal communication.
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63
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(a) Winne, J. M.; Guang, B.; D'Herde, J.; De Clercq, P. J. Org. Lett. 2006, 8, 4815.
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Winne, J.M.1
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De Clercq, P.J.4
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