-
1
-
-
79952528702
-
-
For reaction of cyanogen bromide with aryllithium reagents, see
-
For reaction of cyanogen bromide with aryllithium reagents, see
-
-
-
-
2
-
-
0142068746
-
-
L. A. Paquette, F. Pierre, C. E. Cottrell, J. Am. Chem. Soc. 1987, 109, 5731
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 5731
-
-
Paquette, L.A.1
Pierre, F.2
Cottrell, C.E.3
-
3
-
-
0001455559
-
-
L. A. Paquette, K. S. Learn, J. L. Romine, H. S. Lin, J. Am. Chem. Soc. 1988, 110, 879
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 879
-
-
Paquette, L.A.1
Learn, K.S.2
Romine, J.L.3
Lin, H.S.4
-
4
-
-
0001046408
-
-
J. A. Miller, W. Leong, G. Zweifel, J. Org. Chem. 1988, 53, 1839
-
(1988)
J. Org. Chem.
, vol.53
, pp. 1839
-
-
Miller, J.A.1
Leong, W.2
Zweifel, G.3
-
5
-
-
0037049175
-
-
C. Jaramillo, J. C. Carretero, J. de Diego, M. del Prado, C. Hamdouchi, J. L. Roldán, C. Sánchez-Martinez, Tetrahedron Lett. 2002, 43, 9051
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 9051
-
-
Jaramillo, C.1
Carretero, J.C.2
De Diego, J.3
Del Prado, M.4
Hamdouchi, C.5
Roldán, J.L.6
Sánchez-Martinez, C.7
-
6
-
-
0348048829
-
-
Y. Kobayashi, A. Fukuda, T. Kimachi, M. Ju-ichi, Y. Takemoto, Tetrahedron Lett. 2004, 45, 677
-
(2004)
Tetrahedron Lett.
, vol.45
, pp. 677
-
-
Kobayashi, Y.1
Fukuda, A.2
Kimachi, T.3
Ju-Ichi, M.4
Takemoto, Y.5
-
7
-
-
72049100968
-
-
A. Casoni, G. Celentano, F. Clerici, A. Contini, M. L. Gelmi, G. Mazzeo, S. Pellegrino, C. Rosini, Tetrahedron: Asymmetry 2009, 20, 2247.
-
(2009)
Tetrahedron: Asymmetry
, vol.20
, pp. 2247
-
-
Casoni, A.1
Celentano, G.2
Clerici, F.3
Contini, A.4
Gelmi, M.L.5
Mazzeo, G.6
Pellegrino, S.7
Rosini, C.8
-
8
-
-
0342710062
-
-
T. G. Back, B. P. Dyck, M. Parvez, J. Org. Chem. 1995, 60, 4657.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 4657
-
-
Back, T.G.1
Dyck, B.P.2
Parvez, M.3
-
9
-
-
79952494011
-
-
For preparation of cyanamide from cyanogen bromide, see
-
For preparation of cyanamide from cyanogen bromide, see
-
-
-
-
10
-
-
0018664840
-
-
W. J. Ross, R. G. Harrison, M. R. J. Jolley, M. C. Neville, A. Todd, J. P. Verge, W. Dawson, W. J. F. Sweatman, J. Med. Chem. 1979, 22, 412
-
(1979)
J. Med. Chem.
, vol.22
, pp. 412
-
-
Ross, W.J.1
Harrison, R.G.2
Jolley, M.R.J.3
Neville, M.C.4
Todd, A.5
Verge, J.P.6
Dawson, W.7
Sweatman, W.J.F.8
-
13
-
-
0032900708
-
-
A. Padwa, M. A. Brodney, B. Liu, K. Satake, T. Wu, J. Org. Chem. 1999, 64, 3595
-
(1999)
J. Org. Chem.
, vol.64
, pp. 3595
-
-
Padwa, A.1
Brodney, M.A.2
Liu, B.3
Satake, K.4
Wu, T.5
-
15
-
-
0037040667
-
-
F. M. Rivas, A. J. Giessert, S. T. Diver, J. Org. Chem. 2002, 67, 1708
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1708
-
-
Rivas, F.M.1
Giessert, A.J.2
Diver, S.T.3
-
16
-
-
1842864743
-
-
M. P. Price, W. Guida, T. Jackson, J. Nydick, P. Gladstone, J. Juarez, F. Doñate, R. Ternansky, Bioorg. Med. Chem. 2003, 13, 107
-
(2003)
Bioorg. Med. Chem.
, vol.13
, pp. 107
-
-
Price, M.P.1
Guida, W.2
Jackson, T.3
Nydick, J.4
Gladstone, P.5
Juarez, J.6
Doñate, F.7
Ternansky, R.8
-
18
-
-
18144386189
-
-
R. K. Grover, A. P. Kesarwani, G. K. Srivastava, B. Kundu, R. Roy, Tetrahedron 2005, 61, 5011
-
(2005)
Tetrahedron
, vol.61
, pp. 5011
-
-
Grover, R.K.1
Kesarwani, A.P.2
Srivastava, G.K.3
Kundu, B.4
Roy, R.5
-
19
-
-
20344374157
-
-
Y. Cheng, Q. Zhu, Q. S. Li, O. Meth-Cohn, J. Org. Chem. 2005, 70, 4840
-
(2005)
J. Org. Chem.
, vol.70
, pp. 4840
-
-
Cheng, Y.1
Zhu, Q.2
Li, Q.S.3
Meth-Cohn, O.4
-
20
-
-
19944407105
-
-
D. G. Barrett, D. N. Deaton, A. M. Hassell, R. B. McFadyen, A. B. Miller, L. R. Miller, J. A. Payne, L. M. Shewchuk, J. Willard, L. L. Wright, Bioorg. Med. Chem. 2005, 5, 3039
-
(2005)
Bioorg. Med. Chem.
, vol.5
, pp. 3039
-
-
Barrett, D.G.1
Deaton, D.N.2
Hassell, A.M.3
McFadyen, R.B.4
Miller, A.B.5
Miller, L.R.6
Payne, J.A.7
Shewchuk, L.M.8
Willard, J.9
Wright, L.L.10
-
21
-
-
33846623374
-
-
K. Starcevic, I. Caleta, D. Cincic, B. Kaitner, M. Kralj, K. Ester, G. M. Karminski-Zamola, Heterocycles 2006, 68, 2285
-
(2006)
Heterocycles
, vol.68
, pp. 2285
-
-
Starcevic, K.1
Caleta, I.2
Cincic, D.3
Kaitner, B.4
Kralj, M.5
Ester, K.6
Karminski-Zamola, G.M.7
-
22
-
-
33747397958
-
-
L. Hwang, C. Tus, J. Wang, J. Heterocycl. Chem. 2006, 43, 889
-
(2006)
J. Heterocycl. Chem.
, vol.43
, pp. 889
-
-
Hwang, L.1
Tus, C.2
Wang, J.3
-
23
-
-
33645796932
-
-
U. Köhn, M. Klopfleisch, H. Görls, E. Anders, Tetrahedron: Asymmetry 2006, 17, 811
-
(2006)
Tetrahedron: Asymmetry
, vol.17
, pp. 811
-
-
Köhn, U.1
Klopfleisch, M.2
Görls, H.3
Anders, E.4
-
24
-
-
34548489855
-
-
M. Hasegawa, N. Nishigaki, Y. Washio, K. Kano, P. A. Harris, H. Sato, I. Mori, R. I. West, M. Shibahara, H. Toyoda, L. Wang, R. T. Nolte, J. M. Veal, M. Cheung, J. Med. Chem. 2007, 50, 4453
-
(2007)
J. Med. Chem.
, vol.50
, pp. 4453
-
-
Hasegawa, M.1
Nishigaki, N.2
Washio, Y.3
Kano, K.4
Harris, P.A.5
Sato, H.6
Mori, I.7
West, R.I.8
Shibahara, M.9
Toyoda, H.10
Wang, L.11
Nolte, R.T.12
Veal, J.M.13
Cheung, M.14
-
26
-
-
51349155474
-
-
S. Nag, A. Mishra, S. Batra, Tetrahedron 2008, 64, 10162
-
(2008)
Tetrahedron
, vol.64
, pp. 10162
-
-
Nag, S.1
Mishra, A.2
Batra, S.3
-
27
-
-
70350044659
-
-
M. Saitoh, J. Kunitomo, E. Kimura, H. Iwashita, Y. Uno, T. Onishi, N. Uchiyama, T. Kawamoto, T. Tanaka, C. D. Mol, J. Med. Chem. 2009, 52, 6270.
-
(2009)
J. Med. Chem.
, vol.52
, pp. 6270
-
-
Saitoh, M.1
Kunitomo, J.2
Kimura, E.3
Iwashita, H.4
Uno, Y.5
Onishi, T.6
Uchiyama, N.7
Kawamoto, T.8
Tanaka, T.9
Mol, C.D.10
-
28
-
-
79952502777
-
-
For selected samples of Zincke aldehyde formation involving cyanogen bromide, see
-
For selected samples of Zincke aldehyde formation involving cyanogen bromide, see
-
-
-
-
29
-
-
84966355313
-
-
T. Zincke, G. Heuser, W. Möller, Justus Liebigs Ann. Chem. 1904, 333, 296
-
(1904)
Justus Liebigs Ann. Chem.
, vol.333
, pp. 296
-
-
Zincke, T.1
Heuser, G.2
Möller, W.3
-
32
-
-
79952492013
-
-
For von Braun reactions, see
-
For von Braun reactions, see
-
-
-
-
34
-
-
84981749658
-
-
J. von Braun, K. Heider, E. Müller, Ber. Dtsch. Chem. Ges. 1918, 51, 273
-
(1918)
Ber. Dtsch. Chem. Ges.
, vol.51
, pp. 273
-
-
Von Braun, J.1
Heider, K.2
Müller, E.3
-
37
-
-
0037155514
-
-
S. Chambert, F. Thomasson, J. Décout, J. Org. Chem. 2002, 67, 1898
-
(2002)
J. Org. Chem.
, vol.67
, pp. 1898
-
-
Chambert, S.1
Thomasson, F.2
Décout, J.3
-
38
-
-
23044459107
-
-
R. Leung-Toung, T. F. Tam, Y. Zhao, C. D. Simpson, W. Li, D. Desilets, K. Karimian, J. Org. Chem. 2005, 70, 6230
-
(2005)
J. Org. Chem.
, vol.70
, pp. 6230
-
-
Leung-Toung, R.1
Tam, T.F.2
Zhao, Y.3
Simpson, C.D.4
Li, W.5
Desilets, D.6
Karimian, K.7
-
39
-
-
58049221259
-
-
W. S. McCall, T. A. Grillo, D. L. Comins, J. Org. Chem. 2008, 73, 9744
-
(2008)
J. Org. Chem.
, vol.73
, pp. 9744
-
-
McCall, W.S.1
Grillo, T.A.2
Comins, D.L.3
-
40
-
-
73449114976
-
-
R. L. Giles, R. A. Nkansah, R. E. Looper, J. Org. Chem. 2010, 75, 261
-
(2010)
J. Org. Chem.
, vol.75
, pp. 261
-
-
Giles, R.L.1
Nkansah, R.A.2
Looper, R.E.3
-
41
-
-
77951294759
-
-
Y. Hayashi, T. Kumamoto, M. Kawahata, K. Yamaguchi, T. Ishikawa, Tetrahedron 2010, 66, 3836.
-
(2010)
Tetrahedron
, vol.66
, pp. 3836
-
-
Hayashi, Y.1
Kumamoto, T.2
Kawahata, M.3
Yamaguchi, K.4
Ishikawa, T.5
-
42
-
-
53849099686
-
-
A. Trofimov, N. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 13538.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 13538
-
-
Trofimov, A.1
Chernyak, N.2
Gevorgyan, V.3
-
43
-
-
79952504125
-
-
In the test experiment, the commercially available α-bromoketone 3, upon treatment with NaCN, was quantitatively converted into cyanoepoxide 2 a. For formation of epoxides via an addition/substitution process of nucleophiles with α-halo ketones, see
-
In the test experiment, the commercially available α-bromoketone 3, upon treatment with NaCN, was quantitatively converted into cyanoepoxide 2 a. For formation of epoxides via an addition/substitution process of nucleophiles with α-halo ketones, see
-
-
-
-
46
-
-
79952506090
-
-
A certain amount of cyclopentenyl and cyclohexenyl phenones was observed by GC-MS analysis of the crude reaction mixtures.
-
A certain amount of cyclopentenyl and cyclohexenyl phenones was observed by GC-MS analysis of the crude reaction mixtures.
-
-
-
-
47
-
-
79952525071
-
-
Cyanoepoxidation of ketone 1 h produced an inseparable mixture of diastereomers 2 h. See the Supporting Information for details.
-
Cyanoepoxidation of ketone 1 h produced an inseparable mixture of diastereomers 2 h. See the Supporting Information for details.
-
-
-
-
48
-
-
79952505875
-
-
Fully aliphatic ketones appeared to be unstable under these reaction conditions.
-
Fully aliphatic ketones appeared to be unstable under these reaction conditions.
-
-
-
-
49
-
-
79952503904
-
-
For selected examples on the preparation of cyanoepoxides, see
-
For selected examples on the preparation of cyanoepoxides, see
-
-
-
-
50
-
-
17044374655
-
-
M.-X. Wang, G. Deng, D.-X. Wang, Q.-Y. Zheng, J. Org. Chem. 2005, 70, 2439
-
(2005)
J. Org. Chem.
, vol.70
, pp. 2439
-
-
Wang, M.-X.1
Deng, G.2
Wang, D.-X.3
Zheng, Q.-Y.4
-
51
-
-
0037178550
-
-
N. F. Badham, W. L. Mendelson, A. Allen, A. M. Diederich, D. S. Eggleston, J. J. Filan, A. J. Freyer, A. J. Killmer, C. J. Kowalski, L. Liu, V. J. Novack, F. G. Vogt, K. S. Webb, J. Yang, J. Org. Chem. 2002, 67, 5440
-
(2002)
J. Org. Chem.
, vol.67
, pp. 5440
-
-
Badham, N.F.1
Mendelson, W.L.2
Allen, A.3
Diederich, A.M.4
Eggleston, D.S.5
Filan, J.J.6
Freyer, A.J.7
Killmer, A.J.8
Kowalski, C.J.9
Liu, L.10
Novack, V.J.11
Vogt, F.G.12
Webb, K.S.13
Yang, J.14
-
52
-
-
0035851385
-
-
K. A. Bhatia, K. J. Eash, N. M. Leonard, M. C. Oswald, R. S. Mohan, Tetrahedron Lett. 2001, 42, 8129
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 8129
-
-
Bhatia, K.A.1
Eash, K.J.2
Leonard, N.M.3
Oswald, M.C.4
Mohan, R.S.5
-
53
-
-
6444226688
-
-
see also
-
A. E. Lurain, A. Maestri, A. R. Kelly, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc. 2004, 126, 13608; see also
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13608
-
-
Lurain, A.E.1
Maestri, A.2
Kelly, A.R.3
Carroll, P.J.4
Walsh, P.J.5
-
54
-
-
84885766488
-
-
in (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, pp. .
-
V. K. Aggarwal, D. M. Badine, V. A. Moorthie, in Aziridines and Epoxides in Organic Synthesis (Ed.:, A. K. Yudin,), Wiley-VCH, Weinheim, 2006, pp. 1.
-
(2006)
Aziridines and Epoxides in Organic Synthesis
, pp. 1
-
-
Aggarwal, V.K.1
Badine, D.M.2
Moorthie, V.A.3
-
55
-
-
79952506970
-
-
For selected examples on using fully substituted cyanoepoxides in synthesis, see
-
For selected examples on using fully substituted cyanoepoxides in synthesis, see
-
-
-
-
56
-
-
79952505641
-
-
(Alembic Limited, India), EP1249447 (A1)
-
D. M. Rathod, S. Rengaraju, M. M. Gharpure, N. M. Patel, M. M. Deoahar, (Alembic Limited, India), EP1249447 (A1), 2002
-
(2002)
-
-
Rathod, D.M.1
Rengaraju, S.2
Gharpure, M.M.3
Patel, N.M.4
Deoahar, M.M.5
-
57
-
-
0029877997
-
-
M. Aiai, M. Baudy-Floch, A. Robert, P. Le Grel, Synthesis 1996, 403
-
(1996)
Synthesis
, pp. 403
-
-
Aiai, M.1
Baudy-Floch, M.2
Robert, A.3
Le Grel, P.4
-
59
-
-
0000491726
-
-
G. Stork, W. S. Worrall, J. J. Pappas, J. Am. Chem. Soc. 1960, 82, 4315.
-
(1960)
J. Am. Chem. Soc.
, vol.82
, pp. 4315
-
-
Stork, G.1
Worrall, W.S.2
Pappas, J.J.3
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