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1
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45649084545
-
-
Taken in part from: Wei, Y. M.S. Thesis, Duquesne University, Pittsburgh, PA, 2007.
-
Taken in part from: Wei, Y. M.S. Thesis, Duquesne University, Pittsburgh, PA, 2007.
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6
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0033556019
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37049107708
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29
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0000576324
-
-
The bond length is the mean of CN distance obtained from 5059 nitriles in the Cambridge Structural Database
-
Le Questel J.-Y., Berthelot M., and Laurence C. J. Phys. Org. Chem. 13 (2000) 347 The bond length is the mean of CN distance obtained from 5059 nitriles in the Cambridge Structural Database
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Le Questel, J.-Y.1
Berthelot, M.2
Laurence, C.3
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30
-
-
45649084647
-
-
Nitriles are powerful inductive stabilizing groups with weak delocalizing effects:
-
Nitriles are powerful inductive stabilizing groups with weak delocalizing effects:
-
-
-
-
34
-
-
11344284526
-
-
Typically the C-CN bond lengths (1.36-1.40 Å) are close to those found in benzene derivatives (1.38 Å):
-
Typically the C-CN bond lengths (1.36-1.40 Å) are close to those found in benzene derivatives (1.38 Å):. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. J. Chem. Soc., Perkin Trans. 2 (1987) 1
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(1987)
J. Chem. Soc., Perkin Trans. 2
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Allen, F.H.1
Kennard, O.2
Watson, D.G.3
Brammer, L.4
Orpen, A.G.5
Taylor, R.6
-
35
-
-
45649083172
-
-
Nitriles are powerful inductive stabilizing groups with weak delocalizing effects:
-
Nitriles are powerful inductive stabilizing groups with weak delocalizing effects:
-
-
-
-
36
-
-
45649083235
-
-
See Ref. 7a;
-
See Ref. 7a;
-
-
-
-
37
-
-
45649084584
-
-
See Ref. 7b;
-
See Ref. 7b;
-
-
-
-
38
-
-
45649085369
-
-
See Ref. 7c.
-
See Ref. 7c.
-
-
-
-
41
-
-
2542514849
-
-
Fluxional mixtures of N- and C-metalated nitriles are observed in some instances:
-
Fluxional mixtures of N- and C-metalated nitriles are observed in some instances:. Sott R., Granander J., and Hilmersson G. J. Am. Chem. Soc. 126 (2004) 6798
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(2004)
J. Am. Chem. Soc.
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Sott, R.1
Granander, J.2
Hilmersson, G.3
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49
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34147107497
-
-
For an excellent extension, see:
-
For an excellent extension, see:. Carlier P.R., and Zhang Y. Org. Lett. 9 (2007) 1319
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(2007)
Org. Lett.
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-
Carlier, P.R.1
Zhang, Y.2
-
51
-
-
45649083887
-
-
Subsequent approaches to chiral metalated nitriles have employed non-covalently linked chiral additives:
-
Subsequent approaches to chiral metalated nitriles have employed non-covalently linked chiral additives:
-
-
-
-
52
-
-
0141631816
-
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Suto Y., Kumagai N., Matsunaga S., Kanai M., and Shibasaki M. Org. Lett. 5 (2003) 3147
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(2003)
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Suto, Y.1
Kumagai, N.2
Matsunaga, S.3
Kanai, M.4
Shibasaki, M.5
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53
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0031702860
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Carlier P.R., Lam W.W.-F., Wan N.C., and Williams I.D. Angew. Chem., Int. Ed. 37 (1998) 2252
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Carlier, P.R.1
Lam, W.W.-F.2
Wan, N.C.3
Williams, I.D.4
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57
-
-
45649084636
-
-
For metalated nitriles containing chiral auxiliaries, see:
-
For metalated nitriles containing chiral auxiliaries, see:
-
-
-
-
59
-
-
15444380217
-
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Roux M.-C., Patel S., Mérienne C., Morgant G., and Wartski L. Bull. Chem. Soc. Fr. 134 (1997) 809
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Roux, M.-C.1
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Mérienne, C.3
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0000782851
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Enders D., Lotter H., Maigrot N., Mazaleyrat J.-P., and Welvart Z. Nouv. J. Chim. 8 (1984) 747
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Enders, D.1
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Welvart, Z.5
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73
-
-
45649084130
-
-
Chelation of nitriles by lithium cations is directly analagous to the chelation of organolithiums with proximal alkenes and aromatic π systems:
-
Chelation of nitriles by lithium cations is directly analagous to the chelation of organolithiums with proximal alkenes and aromatic π systems:
-
-
-
-
76
-
-
0000576830
-
-
Bailey W.F., Khanolkar A.D., Gavaskar K., Ovaska T.V., Rossi K., Thiel Y., and Wiberg K.B. J. Am. Chem. Soc. 113 (1991) 5720
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Bailey, W.F.1
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77
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33846965282
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Fleming F.F., Vu V.A., Shook B.C., Raman M., and Steward O.W. J. Org. Chem. 72 (2007) 1431
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Fleming, F.F.1
Vu, V.A.2
Shook, B.C.3
Raman, M.4
Steward, O.W.5
-
78
-
-
45649085229
-
-
Metalated nitriles are more electron rich than their neutral parent nitriles:
-
Metalated nitriles are more electron rich than their neutral parent nitriles:
-
-
-
-
80
-
-
13644270486
-
-
Groux L.F., Weiss T., Reddy D.N., Chase P.A., Piers W.E., Ziegler T., Parvez M., and Benet-Buchholz J. J. Am. Chem. Soc. 127 (2005) 1854
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Groux, L.F.1
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Chase, P.A.4
Piers, W.E.5
Ziegler, T.6
Parvez, M.7
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87
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33746151286
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Hu Y., Bishop R.L., Luxenburger A., Dong S., and Paquette L.A. Org. Lett. 8 (2006) 2735
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(2006)
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Hu, Y.1
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90
-
-
34547408393
-
-
For a preliminary communication, see:
-
For a preliminary communication, see:. Fleming F.F., Wei Y., Liu W., and Zhang Z. Org. Lett. 9 (2007) 2733
-
(2007)
Org. Lett.
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-
Fleming, F.F.1
Wei, Y.2
Liu, W.3
Zhang, Z.4
-
98
-
-
45649084665
-
-
See Ref. 28a;
-
See Ref. 28a;
-
-
-
-
99
-
-
45649083568
-
-
See Ref. 28b.
-
See Ref. 28b.
-
-
-
-
100
-
-
33947459122
-
-
Grignard reagents tend to react with alkylnitriles causing deprotonation and addition:
-
Grignard reagents tend to react with alkylnitriles causing deprotonation and addition:. Reynolds G.A., Humphlett W.J., Swamer F.W., and Hauser C.R. J. Org. Chem. 16 (1950) 165
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(1950)
J. Org. Chem.
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-
Reynolds, G.A.1
Humphlett, W.J.2
Swamer, F.W.3
Hauser, C.R.4
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102
-
-
0033522843
-
-
For an excellent overview of terms, steric constraints, and orbital overlap, see:
-
For an excellent overview of terms, steric constraints, and orbital overlap, see:. Gawley R.E. Tetrahedron Lett. 40 (1999) 4297
-
(1999)
Tetrahedron Lett.
, vol.40
, pp. 4297
-
-
Gawley, R.E.1
-
103
-
-
0038136138
-
-
cis-Decalin 20 exhibited spectral data identical to that of material previously synthesized and shown to have the cis-stereochemistry:
-
cis-Decalin 20 exhibited spectral data identical to that of material previously synthesized and shown to have the cis-stereochemistry:. Fleming F.F., Zhiyu Z., Wang Q., and Steward O.W. Org. Lett. 4 (2002) 2493
-
(2002)
Org. Lett.
, vol.4
, pp. 2493
-
-
Fleming, F.F.1
Zhiyu, Z.2
Wang, Q.3
Steward, O.W.4
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104
-
-
0019191856
-
-
Bernady K.F., Poletto J.F., Nocera J., Mirando P., Schaub R.E., and Weiss M.J. J. Org. Chem. 45 (1980) 4702
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(1980)
J. Org. Chem.
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-
Bernady, K.F.1
Poletto, J.F.2
Nocera, J.3
Mirando, P.4
Schaub, R.E.5
Weiss, M.J.6
-
105
-
-
4544304795
-
-
Fleming F.F., Zhang Z., Wang Q., and Steward O.W. Angew. Chem., Int. Ed. 43 (2004) 1126
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1126
-
-
Fleming, F.F.1
Zhang, Z.2
Wang, Q.3
Steward, O.W.4
-
106
-
-
45649084043
-
-
note
-
29
-
-
-
-
111
-
-
45649083256
-
-
note
-
The authors have deposited the crystallographic data with the Cambridge Crystallographic Data Center. The data can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK.
-
-
-
-
112
-
-
45649085184
-
-
See Ref. 36.
-
See Ref. 36.
-
-
-
-
113
-
-
45649084978
-
-
For related cyclizations of hydroxynitriles, see:
-
For related cyclizations of hydroxynitriles, see:
-
-
-
-
115
-
-
0037070581
-
-
Nicolaou K.C., Baran P.S., Zhong Y.-L., Fong K.C., and Choi H.-S. J. Am. Chem. Soc. 124 (2002) 2190
-
(2002)
J. Am. Chem. Soc.
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-
Nicolaou, K.C.1
Baran, P.S.2
Zhong, Y.-L.3
Fong, K.C.4
Choi, H.-S.5
-
122
-
-
45649084100
-
-
note
-
Formation of lactone 30 establishes the trans-decalin ring-junction stereochemistry.
-
-
-
-
123
-
-
45649083635
-
-
The relative stabilities of cis- and trans-hydrindanes depends on temperature and substitution pattern, with angularly substituted cis-hydrindanes generally being more stable than their trans-hydrindane counterparts:
-
The relative stabilities of cis- and trans-hydrindanes depends on temperature and substitution pattern, with angularly substituted cis-hydrindanes generally being more stable than their trans-hydrindane counterparts:
-
-
-
-
124
-
-
0003942864
-
-
Wiley, New York, NY pp 774-775
-
Eliel E.L., Wilen S.H., and Mander L.N. Stereochemistry of Organic Compounds (1994), Wiley, New York, NY pp 774-775
-
(1994)
Stereochemistry of Organic Compounds
-
-
Eliel, E.L.1
Wilen, S.H.2
Mander, L.N.3
-
126
-
-
45649085047
-
-
note
-
4 afforded chloride 43 accompanied by significant amounts of a material tentatively identified as the ether resulting from internal alcohol attack onto the intermediate phosphonium salt.
-
-
-
-
127
-
-
45649085558
-
-
note
-
22
-
-
-
-
128
-
-
0141645562
-
-
Knochel P., Dohle W., Kneisel F.F., Korn T., and Vu V.A. Angew. Chem., Int. Ed. 42 (2003) 4302
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(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 4302
-
-
Knochel, P.1
Dohle, W.2
Kneisel, F.F.3
Korn, T.4
Vu, V.A.5
-
129
-
-
45649083674
-
-
note
-
The identity of the lactone was unequivocally determined by X-ray crystallography.
-
-
-
-
130
-
-
45549122278
-
-
note
-
45
-
-
-
-
132
-
-
45649085327
-
-
note
-
13C chemical shift comparisons with those of the corresponding decalins.
-
-
-
-
134
-
-
45649084565
-
-
note
-
1H NMR signal for quaternary methyl group.
-
-
-
-
135
-
-
45649083769
-
-
See Ref. 36.
-
See Ref. 36.
-
-
-
-
136
-
-
0004293179
-
-
Oxford University Press, Oxford pp 38-40
-
Kirby A.J. Stereoelectronic Effects (1996), Oxford University Press, Oxford pp 38-40
-
(1996)
Stereoelectronic Effects
-
-
Kirby, A.J.1
-
138
-
-
45649084757
-
-
See Ref. 29.
-
See Ref. 29.
-
-
-
-
140
-
-
45649085312
-
-
See Ref. 27.
-
See Ref. 27.
-
-
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