-
1
-
-
0003581236
-
-
Shono, T.; Kimura, M.; Ito, Y.; Nishida, K.; Oda, R. Bull Chem. Soc. Jpn., 1964, 37, 635.
-
(1964)
Bull Chem. Soc. Jpn
, vol.37
, pp. 635
-
-
Shono, T.1
Kimura, M.2
Ito, Y.3
Nishida, K.4
Oda, R.5
-
2
-
-
0002002167
-
Useful Traps in Radical Chemistry
-
For a review on the behavior of isonitriles as radical traps, see:, Renaud, P, Sibi, M. P. Eds, Wiley-VCH: Weinheim
-
For a review on the behavior of isonitriles as radical traps, see: Nanni, D. Isonitriles: Useful Traps in Radical Chemistry, in Radicals in Organic Synthesis, Renaud, P.; Sibi, M. P. Eds.; Wiley-VCH: Weinheim, 2001, Vol. 2, pp. 44-61.
-
(2001)
Radicals in Organic Synthesis
, vol.2
, pp. 44-61
-
-
Nanni, D.I.1
-
4
-
-
85196434030
-
-
Bishop, R. Ritter-type Reactions, in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; 6, Chap. 1.9.4.2, Refs. 237-242.
-
Bishop, R. Ritter-type Reactions, in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 6, Chap. 1.9.4.2, Refs. 237-242.
-
-
-
-
5
-
-
85196434552
-
-
Although imidoyl radicals are bona fide intermediates in such processes, and they were also detected and studied by EPR specroscopy see Section 2, Kim suggested that the isonitrile/nitrile isomerization could be a concerted process, occurring through a polar transition state, when a particular stable radical, such as benzyl, can be released by β-fragmentation; see his papers on the addition of phenyl anq tributyltin radicals to benzyl isonitrile: Kim, S. S, Lee, K. S, Hwang, S. B, Kim, H. J. Tetrahedron Lett, 1990, 31, 3575;
-
Although imidoyl radicals are bona fide intermediates in such processes, and they were also detected and studied by EPR specroscopy (see Section 2), Kim suggested that the isonitrile/nitrile isomerization could be a concerted process, occurring through a polar transition state, when a particular stable radical, such as benzyl, can be released by β-fragmentation; see his papers on the addition of phenyl anq tributyltin radicals to benzyl isonitrile: Kim, S. S.; Lee, K. S.; Hwang, S. B.; Kim, H. J. Tetrahedron Lett., 1990, 31, 3575;
-
-
-
-
6
-
-
0000309470
-
-
Kim, S. S.; Yang, K. W.; Lee, C. S. J. Org. Chem., 1996, 61, 4827.
-
(1996)
J. Org. Chem
, vol.61
, pp. 4827
-
-
Kim, S.S.1
Yang, K.W.2
Lee, C.S.3
-
8
-
-
0000261977
-
-
Saegusa, T.; Kobayashi, S.; Ito, Y.; Yasuda, N. J. Am. Chem. Soc., 1968, 90, 4182.
-
(1968)
Am. Chem. Soc
, vol.90
, pp. 4182
-
-
Saegusa, T.1
Kobayashi, S.2
Ito, Y.3
Yasuda, N.J.4
-
9
-
-
0003504011
-
-
Saegusa, T.; Ito, Y.; Yasuda, N.; Hotaka, T. J. Org. Chem., 1970, 35, 4238.
-
(1970)
J. Org. Chem
, vol.35
, pp. 4238
-
-
Saegusa, T.1
Ito, Y.2
Yasuda, N.3
Hotaka, T.4
-
10
-
-
0001226141
-
-
(a) Saegusa, T.; Kobayashi, S.; Yoshihiko, I. J. Org. Chem., 1970, 35, 2118;
-
(1970)
J. Org. Chem
, vol.35
, pp. 2118
-
-
Saegusa, T.1
Kobayashi, S.2
Yoshihiko, I.3
-
15
-
-
85196435682
-
-
Additional studies on imidoyls arising from addition of other radicals (silicon- [9e], phosphorus-, and tin-centered radicals) to isonitriles will be dealt with in the next Sections.
-
Additional studies on imidoyls arising from addition of other radicals (silicon- [9e], phosphorus-, and tin-centered radicals) to isonitriles will be dealt with in the next Sections.
-
-
-
-
16
-
-
85196435674
-
-
The only exception is addition of methylsulfanyl radical to tert-butyl isonitrile, which gives methyl thiocyanate and tert-butyl radical instead of tert-butyl isothiocyanate and methyl radical, due to the very strong S-Me bond of the intermediate imidoyl radical (see Ref. 20b below).
-
The only exception is addition of methylsulfanyl radical to tert-butyl isonitrile, which gives methyl thiocyanate and tert-butyl radical instead of tert-butyl isothiocyanate and methyl radical, due to the very strong S-Me bond of the intermediate imidoyl radical (see Ref. 20b below).
-
-
-
-
19
-
-
0345486252
-
-
(c) Kim, S. S.; Koo, H. M.; Choi, S. Y. Tetrahedron Lett., 1985, 26, 891.
-
(1985)
Tetrahedron Lett
, vol.26
, pp. 891
-
-
Kim, S.S.1
Koo, H.M.2
Choi, S.Y.3
-
20
-
-
85196433595
-
-
Abstraction of an iminic hydrogen was also observed to occur intramolecululy by 1,5-H transfer to an aryl radical, see: Gioanola, M.; Leardini, R.; Nanni, D.; Pareschi, P.; Zanardi, G. Tetrahedron, 1995, 51, 2039.
-
Abstraction of an iminic hydrogen was also observed to occur intramolecululy by 1,5-H transfer to an aryl radical, see: Gioanola, M.; Leardini, R.; Nanni, D.; Pareschi, P.; Zanardi, G. Tetrahedron, 1995, 51, 2039.
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-
-
-
21
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-
0030599661
-
-
(a) Nanni, D.; Pareschi, P.; Tundo, A. Tetrahedron Lett., 1996, 37, 9337;
-
(1996)
Tetrahedron Lett
, vol.37
, pp. 9337
-
-
Nanni, D.1
Pareschi, P.2
Tundo, A.3
-
22
-
-
85196434647
-
-
for another α-fragmentation of α-(triphenylmethyl)imidoyl radicals, see
-
for another α-fragmentation of α-(triphenylmethyl)imidoyl radicals, see Ref. 47 below.
-
47 below
-
-
Ref1
-
23
-
-
85196432880
-
-
3SiNC and tert-Bu radical has been proposed by Ingold to explain the radicals detected in die addition of trimethylsilyl radicals to pivalonitrile; see: (b) Kaba, R. A.; Griller, D.; Ingold, K. U. J. Am. Chem. Soc., 1974, 96, 6202.
-
3SiNC and tert-Bu radical has been proposed by Ingold to explain the radicals detected in die addition of trimethylsilyl radicals to pivalonitrile; see: (b) Kaba, R. A.; Griller, D.; Ingold, K. U. J. Am. Chem. Soc., 1974, 96, 6202.
-
-
-
-
24
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-
0034607923
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-
Leardini, R.; Nanni, D.; Zanardi, G. J. Org. Chem., 2000, 65, 2763.
-
(2000)
J. Org. Chem
, vol.65
, pp. 2763
-
-
Leardini, R.1
Nanni, D.2
Zanardi, G.3
-
28
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-
85196434990
-
-
For an additional EPR study on radicals generated from imines, see: Nanni, D, Pareschi, P, Walton, J. C. J. Chem. Soc. Perkin Trans. 2, 2002, 1098. In this paper, however, detection of imidoyls was hindered by competing addition of tert-butoxy radicals to the parent imines, giving aminyls and nitroxides. DFT calculations were also performed in order to show that α-scission of imidoyls is strongly endothermic, even when a tert-butyl radical can be released. A C-unsubstituted imidoyl radical was instead observed by Roberts in the reaction of DTBP with N-methylene-tert-butylamine Ref. 20 c below
-
For an additional EPR study on radicals generated from imines, see: Nanni, D.; Pareschi, P.; Walton, J. C. J. Chem. Soc. Perkin Trans. 2, 2002, 1098. In this paper, however, detection of imidoyls was hindered by competing addition of tert-butoxy radicals to the parent imines, giving aminyls and nitroxides. DFT calculations were also performed in order to show that α-scission of imidoyls is strongly endothermic, even when a tert-butyl radical can be released. A C-unsubstituted imidoyl radical was instead observed by Roberts in the reaction of DTBP with N-methylene-tert-butylamine (Ref. 20 c below).
-
-
-
-
38
-
-
85196432836
-
-
For comparison purpose, Roberts generated some imidoyls also by hydrogen abstraction from imidates or imines by photolysis with bis(trimethylsilyl) or dicumyl peroxide (Refs. 20a,b).
-
For comparison purpose, Roberts generated some imidoyls also by hydrogen abstraction from imidates or imines by photolysis with bis(trimethylsilyl) or dicumyl peroxide (Refs. 20a,b).
-
-
-
-
39
-
-
85196433650
-
-
-1 at 300 K). See: Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc., 1983, 105, 3292.
-
-1 at 300 K). See: Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc., 1983, 105, 3292.
-
-
-
-
40
-
-
0000700297
-
-
Griller, D.; Cooper, J. W.; Ingold, K. U. J. Am. Chem. Soc., 1975, 97, 4269.
-
(1975)
J. Am. Chem. Soc
, vol.97
, pp. 4269
-
-
Griller, D.1
Cooper, J.W.2
Ingold, K.U.3
-
42
-
-
85196432502
-
-
Some other phosphorus-substituted imidoyls were also reported in Ref. 20b.
-
Some other phosphorus-substituted imidoyls were also reported in Ref. 20b.
-
-
-
-
43
-
-
0035917356
-
-
Tichy, S. E.; Thoen, K. K.; Price, J. M.; Ferra, J. J., Jr.; Petucci, C. J.; Kenttämaa, H. I. J. Org. Chem., 2001, 66, 2726.
-
(2001)
J. Org. Chem
, vol.66
, pp. 2726
-
-
Tichy, S.E.1
Thoen, K.K.2
Price, J.M.3
Ferra Jr., J.J.4
Petucci, C.J.5
Kenttämaa, H.I.6
-
44
-
-
85196434572
-
-
Imidoyl radicals could also be formed by Group 11 metal atoms addition to isonitriles in a rotating cryostat at 77 K. However, if ever formed, they seem extremely prone to fragmentation and could not be observed even at so low temperatures. See: Howard, J. A.; Sutcliffe, R.; Dahmane, H.; Mile, B. Organometallics, 1985, 4, 697.
-
Imidoyl radicals could also be formed by Group 11 metal atoms addition to isonitriles in a rotating cryostat at 77 K. However, if ever formed, they seem extremely prone to fragmentation and could not be observed even at so low temperatures. See: Howard, J. A.; Sutcliffe, R.; Dahmane, H.; Mile, B. Organometallics, 1985, 4, 697.
-
-
-
-
45
-
-
0141516243
-
-
(a) Minozzi, M.; Nanni, D.; Walton, J. C. Org. Lett., 2003, 5, 901;
-
(2003)
Org. Lett
, vol.5
, pp. 901
-
-
Minozzi, M.1
Nanni, D.2
Walton, J.C.3
-
46
-
-
1642329299
-
-
(b) Minozzi, M.; Nanni, D.; Walton, J. C. J. Org. Chem., 2004, 69, 2056.
-
(2004)
J. Org. Chem
, vol.69
, pp. 2056
-
-
Minozzi, M.1
Nanni, D.2
Walton, J.C.3
-
47
-
-
0032541682
-
-
De Boeck, B.; Herbert, N.; Pattenden, G. Tetrahedron Lett., 1998, 39, 6971;
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 6971
-
-
De Boeck, B.1
Herbert, N.2
Pattenden, G.3
-
49
-
-
0034829343
-
-
Yamago, S.; Miyazoe, H.; Goto, R.; Hashidume, M.; Sawazaki, T.; Yoshida, J.-I. J. Am. Chem. Soc., 2001, 123, 3697.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 3697
-
-
Yamago, S.1
Miyazoe, H.2
Goto, R.3
Hashidume, M.4
Sawazaki, T.5
Yoshida, J.-I.6
-
50
-
-
37049112394
-
-
(a) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc. Chem. Commun., 1984, 1320;
-
(1984)
J. Chem. Soc. Chem. Commun
, pp. 1320
-
-
Leardini, R.1
Pedulli, G.F.2
Tundo, A.3
Zanardi, G.4
-
51
-
-
37049070160
-
-
(b) Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc. Perkin Trans. 1, 1986, 1591;
-
(1986)
J. Chem. Soc. Perkin Trans. 1
, pp. 1591
-
-
Leardini, R.1
Nanni, D.2
Pedulli, G.F.3
Tundo, A.4
Zanardi, G.5
-
52
-
-
0001255958
-
-
(c) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital., 1989, 119, 637.
-
(1989)
Gazz. Chim. Ital
, vol.119
, pp. 637
-
-
Leardini, R.1
Nanni, D.2
Tundo, A.3
Zanardi, G.4
-
53
-
-
85196435030
-
-
This rearrangement may involve either 3-exo ring closure of the cyclohexadienyl radical onto the C=N double bond, followed by ring opening, or direct C-N bond fragmentation, followed by cyclization of the resulting iminyl radical. Some results (see Ref. 14a) indicate that the latter mechanism is a viable pathway, although the concomitant occurrence of the former cannot be excluded
-
This rearrangement may involve either 3-exo ring closure of the cyclohexadienyl radical onto the C=N double bond, followed by ring opening, or direct C-N bond fragmentation, followed by cyclization of the resulting iminyl radical. Some results (see Ref. 14a) indicate that the latter mechanism is a viable pathway, although the concomitant occurrence of the former cannot be excluded.
-
-
-
-
54
-
-
37049082267
-
-
Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun., 1989, 757.
-
(1989)
J. Chem. Soc., Chem. Commun
, pp. 757
-
-
Leardini, R.1
Nanni, D.2
Tundo, A.3
Zanardi, G.4
-
55
-
-
0002748517
-
-
Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. Synthesis, 1985, 107.
-
(1985)
Synthesis
, pp. 107
-
-
Leardini, R.1
Pedulli, G.F.2
Tundo, A.3
Zanardi, G.4
-
56
-
-
0028843541
-
-
(a) Guidotti, S.; Leardini, R.; Nanni, D.; Pareschi, P.; Zanardi, G. Tetrahedron Lett., 1995, 36, 451;
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 451
-
-
Guidotti, S.1
Leardini, R.2
Nanni, D.3
Pareschi, P.4
Zanardi, G.5
-
57
-
-
0028823626
-
-
(b) Leardini, R.; McNab, H.; Nanni, D. Tetrahedron, 1995, 51, 12143.
-
(1995)
Tetrahedron
, vol.51
, pp. 12143
-
-
Leardini, R.1
McNab, H.2
Nanni, D.3
-
58
-
-
85196433285
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-
Benzoxazoles and biaryls were additional products isolated in trace amounts and symptomatic of the presence of phenoxyl 14: the former are formed by cyclization of the phenoxyl onto the C=N double bond, followed by release of an aryl radical; the latter are the result of attack of that aryl radical onto the solvent benzene
-
Benzoxazoles and biaryls were additional products isolated in trace amounts and symptomatic of the presence of phenoxyl 14: the former are formed by cyclization of the phenoxyl onto the C=N double bond, followed by release of an aryl radical; the latter are the result of attack of that aryl radical onto the solvent benzene.
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-
-
-
59
-
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85196432884
-
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Leardini, R.; Nanni, D.; Santori, M.; Zanardi, G. Tetrahedron, 1992, 48, 3961. For a theoretical study on the competition between imidoyl. radical cyclization onto cyano and sulfide moieties, see Ref. 57c below.
-
Leardini, R.; Nanni, D.; Santori, M.; Zanardi, G. Tetrahedron, 1992, 48, 3961. For a theoretical study on the competition between imidoyl. radical cyclization onto cyano and sulfide moieties, see Ref. 57c below.
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-
-
-
60
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85196435260
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Hi reaction of imidoyls at the sulfur atom strictly resembles that of akin vinyl radicals, which have been shown to release from sulfur acyl Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari; S. Org. Lett., 2003, 5, 1313;
-
Hi reaction of imidoyls at the sulfur atom strictly resembles that of akin vinyl radicals, which have been shown to release from sulfur acyl (Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari; S. Org. Lett., 2003, 5, 1313;
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-
-
-
61
-
-
3142711410
-
-
Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo, P.; Zanardi, G. Synlett, 2004, 987),
-
(2004)
Synlett
, pp. 987
-
-
Benati, L.1
Leardini, R.2
Minozzi, M.3
Nanni, D.4
Scialpi, R.5
Spagnolo, P.6
Zanardi, G.7
-
62
-
-
85196433697
-
-
carbamoyl (Benati, L.; Bencivenni, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo, P.; Zanardi, G. J. Org. Chem, 2006, 71, 3192), and even simple, unstabilized alkyl radicals (Bencivenni, G.; Lanza, T.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Zanardi, G., paper to be subinitted).
-
carbamoyl (Benati, L.; Bencivenni, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo, P.; Zanardi, G. J. Org. Chem, 2006, 71, 3192), and even simple, unstabilized alkyl radicals (Bencivenni, G.; Lanza, T.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Zanardi, G., paper to be subinitted).
-
-
-
-
64
-
-
0001696582
-
-
Dan-oh, Y.; Matta, H.; Uemura, J.; Watanabe, H.; Uneyama, K. Bull. Chem. Soc. Jpn., 1995, 68, 1497.
-
(1995)
Bull. Chem. Soc. Jpn
, vol.68
, pp. 1497
-
-
Dan-oh, Y.1
Matta, H.2
Uemura, J.3
Watanabe, H.4
Uneyama, K.5
-
65
-
-
1242343132
-
-
Curiously, formation of imidoyl halides can also be the fate of imidoyl radicals. In fact, when imidoyls are generated by treatment of isonitriles with alkylmercury halides, they undergo electron transfer to the mercury reagent giving a nitriliurn ion which, in benzene solution, is then trapped by the halide ion. See
-
Curiously, formation of imidoyl halides can also be the fate of imidoyl radicals. In fact, when imidoyls are generated by treatment of isonitriles with alkylmercury halides, they undergo electron transfer to the mercury reagent giving a nitriliurn ion which, in benzene solution, is then trapped by the halide ion. See: Russell, G. A.; Rajaratnam, R.; Chen, P. Acta Chem. Scand., 1998, 52, 528.
-
(1998)
Acta Chem. Scand
, vol.52
, pp. 528
-
-
Russell, G.A.1
Rajaratnam, R.2
Chen, P.3
-
66
-
-
0027493330
-
-
Ueda, Y.; Watanabe, H; Uemura, J.; Uneyama, K. Tetrahedron Lett., 1993, 34, 7933.
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 7933
-
-
Ueda, Y.1
Watanabe, H.2
Uemura, J.3
Uneyama, K.4
-
67
-
-
23644445025
-
-
Kotani, M.; Yamago, S.; Satoh, A.; Tokuyama, H.; Fukuyama, T. Synlett, 2005, 1893.
-
(2005)
Synlett
, pp. 1893
-
-
Kotani, M.1
Yamago, S.2
Satoh, A.3
Tokuyama, H.4
Fukuyama, T.5
-
68
-
-
85196433211
-
-
Some additional examples dealing with the radical chemistry of telluroimidates have been reported: since they involve use of isonitriles, they will be discussed in the next Section (see Refs 66 below).
-
Some additional examples dealing with the radical chemistry of telluroimidates have been reported: since they involve use of isonitriles, they will be discussed in the next Section (see Refs 66 below).
-
-
-
-
70
-
-
4544267705
-
-
(a) Bowman, W. R.; Fletcher, A. J.; Lovell, P. J.; Pedersen, J. M. Synlett, 2004, 1905;
-
(2004)
Synlett
, pp. 1905
-
-
Bowman, W.R.1
Fletcher, A.J.2
Lovell, P.J.3
Pedersen, J.M.4
-
71
-
-
28844491033
-
-
(b) Pedersen, J. M.; Bowman, W. R.; Elsegood, M. R. J.; Fletcher, A. J.; Lovell, P. J. J. Org. Chem., 2005, 70, 10615;
-
(2005)
J. Org. Chem
, vol.70
, pp. 10615
-
-
Pedersen, J.M.1
Bowman, W.R.2
Elsegood, M.R.J.3
Fletcher, A.J.4
Lovell, P.J.5
-
72
-
-
33751532908
-
-
(c) Bowman, W. R.; Fletcher, A. J.; Pedersen, J. M.; Lovell, P. J.; Elsegood, M. R. J.; Lopez, E. H.; McKee, V.; Potts, G. B. S. Tetrahedron, 2007, 63, 191.
-
(2007)
Tetrahedron
, vol.63
, pp. 191
-
-
Bowman, W.R.1
Fletcher, A.J.2
Pedersen, J.M.3
Lovell, P.J.4
Elsegood, M.R.J.5
Lopez, E.H.6
McKee, V.7
Potts, G.B.S.8
-
73
-
-
0035937264
-
-
Fujiwara, S.-I.; Matsuya, T.; Maeda, H.; Shin-ike, T.; Kambe, N.; Sonoda, N. J. Org. Chem., 2001, 66, 2183.
-
(2001)
J. Org. Chem
, vol.66
, pp. 2183
-
-
Fujiwara, S.-I.1
Matsuya, T.2
Maeda, H.3
Shin-ike, T.4
Kambe, N.5
Sonoda, N.6
-
74
-
-
0001451085
-
-
For a very nice review on the use of radical carbonylation in synthesis, see
-
For a very nice review on the use of radical carbonylation in synthesis, see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev., 1996, 96, 177.
-
(1996)
Chem. Rev
, vol.96
, pp. 177
-
-
Ryu, I.1
Sonoda, N.2
Curran, D.P.3
-
77
-
-
0033594438
-
-
(c) Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc., 1999, 121, 3791;
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 3791
-
-
Tokuyama, H.1
Yamashita, T.2
Reding, M.T.3
Kaburagi, Y.4
Fukuyama, T.5
-
79
-
-
0040344639
-
Isonitriles
-
For a general view on isonitrile chemistry, see: a, Patai, S, Rappoport, Z. Eds, Wiley: London, Chap. 15;
-
For a general view on isonitrile chemistry, see: (a) Hoffmann, P.; Marquarding, D.; Kliimann, H.; Ugi, I. Isonitriles, in The Chemistry of the Cyano Group, Patai, S.; Rappoport, Z. Eds.; Wiley: London, 1970; Chap. 15;
-
(1970)
The Chemistry of the Cyano Group
-
-
Hoffmann, P.1
Marquarding, D.2
Kliimann, H.3
Ugi, I.4
-
81
-
-
0000809496
-
Synthesis of Pseudohalides, Nitriles and Related Compounds
-
Trost, B. M, Fleming, I. Eds, Pergamon: Oxford, Chap. 1.8.2;
-
(c) Grashey, R. Synthesis of Pseudohalides, Nitriles and Related Compounds, in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 6, Chap. 1.8.2;
-
(1991)
Comprehensive Organic Synthesis
, vol.6
-
-
Grashey, R.1
-
82
-
-
85196433525
-
-
Kantlehner, W. Synthesis of Iminium Salts, Orthoesters and Related Compounds, ibid.; 6, Chap. 2.7.2. 1.1;
-
(d) Kantlehner, W. Synthesis of Iminium Salts, Orthoesters and Related Compounds, ibid.; Vol. 6, Chap. 2.7.2. 1.1;
-
-
-
-
83
-
-
85196434266
-
-
Chap. 4.6;
-
(e) Ugi, I.; Lohberger, S.; Karl, R. The Passerini and Ugi Reactions, ibid.; Vol. 2, Chap. 4.6;
-
The Passerini and Ugi Reactions, ibid
, vol.2
-
-
Ugi, I.1
Lohberger, S.2
Karl, R.3
-
86
-
-
37049107040
-
-
(a) Barton, D. H. R.; Bringmann, G.; Lamotte, G.; Motherwell, W. B.; Hay Motherwell, R. S.; Porter, A. E. A. J. Chem. Soc. Perkin Trans. 1, 1980, 2657;
-
(1980)
J. Chem. Soc. Perkin Trans. 1
, pp. 2657
-
-
Barton, D.H.R.1
Bringmann, G.2
Lamotte, G.3
Motherwell, W.B.4
Hay Motherwell, R.S.5
Porter, A.E.A.6
-
88
-
-
0025128220
-
-
Chatgilialoglu, C.; Giese, B.; Kopping, B. Tetrahedron Lett., 1990, 31, 6013.
-
(1990)
Tetrahedron Lett
, vol.31
, pp. 6013
-
-
Chatgilialoglu, C.1
Giese, B.2
Kopping, B.3
-
90
-
-
0000874486
-
-
Barton, D. H. R.; Ozbalik, N.; Vacher, B. Tetrahedron, 1988, 44, 3501.
-
(1988)
Tetrahedron
, vol.44
, pp. 3501
-
-
Barton, D.H.R.1
Ozbalik, N.2
Vacher, B.3
-
92
-
-
0001206445
-
-
(b) Curran, D. P.; Sisko, J.; Yeske, P. E.; Liu, H. Pure Appl. Chem., 1993, 65, 1153;
-
(1993)
Pure Appl. Chem
, vol.65
, pp. 1153
-
-
Curran, D.P.1
Sisko, J.2
Yeske, P.E.3
Liu, H.4
-
93
-
-
33751141093
-
-
(c) Curran, D. P.; Ko, S. -B.; Josien, H. Angew. Chem. Int. Ed., 1995, 34, 2683;
-
(1995)
Angew. Chem. Int. Ed
, vol.34
, pp. 2683
-
-
Curran, D.P.1
Ko, S.-B.2
Josien, H.3
-
94
-
-
0030603102
-
-
(d) Curran, D. P.; Liu, H.; Josien, H.; Ko, S. -B. Tetrahedron, 1996, 52, 11385;
-
(1996)
Tetrahedron
, vol.52
, pp. 11385
-
-
Curran, D.P.1
Liu, H.2
Josien, H.3
Ko, S.-B.4
-
96
-
-
0344074659
-
-
(f) Josien, H.; Bom, D.; Curran, D. P.; Zheng, Y. -H.; Chou, T. -C. Bioorg. Med. Chem. Lett., 1997, 7, 3189;
-
(1997)
Bioorg. Med. Chem. Lett
, vol.7
, pp. 3189
-
-
Josien, H.1
Bom, D.2
Curran, D.P.3
Zheng, Y.-H.4
Chou, T.-C.5
-
97
-
-
0031934061
-
-
(g) Josien, H.; Ko, S. -B.; Bom, D.; Curran, D. P. Chem. Eur. J., 1998, 4, 67;
-
(1998)
Chem. Eur. J
, vol.4
, pp. 67
-
-
Josien, H.1
Ko, S.-B.2
Bom, D.3
Curran, D.P.4
-
99
-
-
0029083476
-
-
Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron, 1995, 51, 9045;
-
(1995)
Tetrahedron
, vol.51
, pp. 9045
-
-
Nanni, D.1
Pareschi, P.2
Rizzoli, C.3
Sgarabotto, P.4
Tundo, A.5
-
100
-
-
0032554907
-
-
(b) Camaggi, C. M.; Leardini, R.; Nanni, D.; Zanardi, G. Tetrahedron, 1998, 54, 5587;
-
(1998)
Tetrahedron
, vol.54
, pp. 5587
-
-
Camaggi, C.M.1
Leardini, R.2
Nanni, D.3
Zanardi, G.4
-
101
-
-
0034005803
-
-
(c) Nanni, D.; Calestani, G.; Leardini, R.; Zanardi, G. Eur. J. Org. Chem., 2000, 707.
-
(2000)
Eur. J. Org. Chem
, pp. 707
-
-
Nanni, D.1
Calestani, G.2
Leardini, R.3
Zanardi, G.4
-
102
-
-
85196432451
-
-
A few [4 + 1] annulation strategies involving a cyano group were also used by Curran: see Refs. 56d,g.
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A few [4 + 1] annulation strategies involving a cyano group were also used by Curran: see Refs. 56d,g.
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-
-
-
103
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85196432389
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-
For another example of tandem cyclization triggered by attack of an alkylsulfanyl radical to an isonitrile, see Ref. 73below
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For another example of tandem cyclization triggered by attack of an alkylsulfanyl radical to an isonitrile, see Ref. 73below.
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-
-
-
104
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85196434109
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For another example of attack to aromatic rings of imidoyl radicals generated from isonitriles, see Ref. 35b. In that case, 2-(phenoxy)phenyl isonitrile, when treated with dibenzoyl peroxide, gave 2-phenyloxazole through presumable 1,5-phenyl radical migration (in analogy to what shown in Scheme 15) followed by ring closure of the resulting phenoxyl with expulsion of benzoyloxy radicals.
-
For another example of attack to aromatic rings of imidoyl radicals generated from isonitriles, see Ref. 35b. In that case, 2-(phenoxy)phenyl isonitrile, when treated with dibenzoyl peroxide, gave 2-phenyloxazole through presumable 1,5-phenyl radical migration (in analogy to what shown in Scheme 15) followed by ring closure of the resulting phenoxyl with expulsion of benzoyloxy radicals.
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-
-
-
106
-
-
0000874522
-
-
(a) Bachi, M. D.; Balanov, A.; Bar-Ner, N. J. Org. Chem., 1994, 59, 7752;
-
(1994)
J. Org. Chem
, vol.59
, pp. 7752
-
-
Bachi, M.D.1
Balanov, A.2
Bar-Ner, N.3
-
109
-
-
0029841417
-
-
(d) Bachi, M. D.; Bar-Ner, N.; Melman, A. J. Org. Chem., 1996, 61, 7116.
-
(1996)
J. Org. Chem
, vol.61
, pp. 7116
-
-
Bachi, M.D.1
Bar-Ner, N.2
Melman, A.3
-
110
-
-
85196434636
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-
Another convenient enantioselective total synthesis of (-)α-kainic acid was obtained by tin radical addition to an alkenyl thioformamide, see Ref 49a. Similar cyclizations to thiolactams were also carried by tin radical additions to alkenyl isothiocyanates, see Ref. 76below.
-
Another convenient enantioselective total synthesis of (-)α-kainic acid was obtained by tin radical addition to an alkenyl thioformamide, see Ref 49a. Similar cyclizations to thiolactams were also carried by tin radical additions to alkenyl isothiocyanates, see Ref. 76below.
-
-
-
-
111
-
-
0000352286
-
-
(a) Fukuyama, T.; Chen, X.; Peng, G. J. Am. Chem. Soc., 1994, 116, 3127;
-
(1994)
J. Am. Chem. Soc
, vol.116
, pp. 3127
-
-
Fukuyama, T.1
Chen, X.2
Peng, G.3
-
114
-
-
0033609901
-
-
Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett., 1999, 40, 6325.
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 6325
-
-
Rainier, J.D.1
Kennedy, A.R.2
Chase, E.3
-
115
-
-
0033582993
-
-
(a) Yamago, S.; Miyazoe, H.; Goto, R.; Yoshida, J. -I. Tetrahedron Lett., 1999, 40, 2347;
-
(1999)
Tetrahedron Lett
, vol.40
, pp. 2347
-
-
Yamago, S.1
Miyazoe, H.2
Goto, R.3
Yoshida, J.-I.4
-
116
-
-
0034706349
-
-
(b) Yamago, S.; Miyazoe, H.; Sawazaki, T.; Goto, R.; Yoshida, J. -I. Tetrahedron Lett., 2000, 41, 7517;
-
(2000)
Tetrahedron Lett
, vol.41
, pp. 7517
-
-
Yamago, S.1
Miyazoe, H.2
Sawazaki, T.3
Goto, R.4
Yoshida, J.-I.5
-
117
-
-
0034675634
-
-
(c) Miyazoe, H.; Yamago, S.; Yoshida, J. -I. Angew. Chem. Int. Ed., 2000, 39, 3669;
-
(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 3669
-
-
Miyazoe, H.1
Yamago, S.2
Yoshida, J.-I.3
-
118
-
-
0037414920
-
-
(d) Yamago, S.; Miyazoe, H.; Nakayama, T.; Miyoshi, M.; Yoshida, J. -i. Angew. Chem. Int. Ed., 2003, 42, 117;
-
(2003)
Angew. Chem. Int. Ed
, vol.42
, pp. 117
-
-
Yamago, S.1
Miyazoe, H.2
Nakayama, T.3
Miyoshi, M.4
Yoshida, J.-I.5
-
120
-
-
4544294493
-
-
Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Scialpi, R.; Spagnolo, P.; Strazzari, S.; Zanardi, G. Angew. Chem. Int. Ed., 2004, 43, 3598.
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 3598
-
-
Benati, L.1
Leardini, R.2
Minozzi, M.3
Nanni, D.4
Scialpi, R.5
Spagnolo, P.6
Strazzari, S.7
Zanardi, G.8
-
121
-
-
33846241806
-
-
Tsuchii, K.; Tsuboi, Y.; Kawaguchi, S. -I.; Takahashi, J.; Sonoda, N.; Nomoto, A.; Ogawa, A. J. Org. Chem., 2007, 72, 415.
-
(2007)
J. Org. Chem
, vol.72
, pp. 415
-
-
Tsuchii, K.1
Tsuboi, Y.2
Kawaguchi, S.-I.3
Takahashi, J.4
Sonoda, N.5
Nomoto, A.6
Ogawa, A.7
-
122
-
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85196434885
-
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In some cases, also α-scission of thioimidoyls affording isonitriles can become a competing, dangerous process, see
-
In some cases, also α-scission of thioimidoyls affording isonitriles can become a competing, dangerous process, see: Refs. 52a, 76, and 77a.
-
52a, 76, and 77a
-
-
Refs1
-
123
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85196434368
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The first instances of reactions between isocyanates and isothiocyanates with organostannanes date back to the beginning of the 1960s Lorenz, D. H, Becker, E. I. J. Org. Chem, 1963, 28, 1707;
-
The first instances of reactions between isocyanates and isothiocyanates with organostannanes date back to the beginning of the 1960s (Lorenz, D. H.; Becker, E. I. J. Org. Chem., 1963, 28, 1707;
-
-
-
-
124
-
-
0342353498
-
-
but in those papers no evidence is reported about the intermediacy of radical species
-
Noltes, J. G.; Janssen, M. J. J. Organomet. Chem., 1964, 1, 346), but in those papers no evidence is reported about the intermediacy of radical species.
-
(1964)
J. Organomet. Chem
, vol.1
, pp. 346
-
-
Noltes, J.G.1
Janssen, M.J.2
-
125
-
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85196433805
-
-
See also:, 1413 Section III, Refs. 140-143
-
See also: Crich, D.; Quintero, L. Chem. Rev., 1989, 89, 1413 (Section III, Refs. 140-143).
-
(1989)
Chem. Rev
, vol.89
-
-
Crich, D.1
Quintero, L.2
-
127
-
-
0026561946
-
-
Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. Tetrahedron, 1992, 48, 2613.
-
(1992)
Tetrahedron
, vol.48
, pp. 2613
-
-
Barton, D.H.R.1
Jaszberenyi, J.C.2
Theodorakis, E.A.3
-
128
-
-
85054478258
-
-
Minozzi, M.; Nanni, D.; Zanardi, G.; Calestani, G. Arkivoc, 2006, 6.
-
(2006)
Arkivoc
, pp. 6
-
-
Minozzi, M.1
Nanni, D.2
Zanardi, G.3
Calestani, G.4
-
129
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85196435943
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An analogous process was observed starting from an alkynylaryl isonitrile and cyclohexylsulfanyl radicals
-
An analogous process was observed starting from an alkynylaryl isonitrile and cyclohexylsulfanyl radicals.
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132
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0000136228
-
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(a) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem., 1997, 62, 8394;
-
(1997)
J. Org. Chem
, vol.62
, pp. 8394
-
-
Leardini, R.1
Nanni, D.2
Pareschi, P.3
Tundo, A.4
Zanardi, G.5
-
133
-
-
0034670575
-
-
(b) Benati, L.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Zanardi, G. J. Org. Chem., 2000, 65, 8669;
-
(2000)
J. Org. Chem
, vol.65
, pp. 8669
-
-
Benati, L.1
Leardini, R.2
Minozzi, M.3
Nanni, D.4
Spagnolo, P.5
Zanardi, G.6
-
134
-
-
0242668707
-
-
(c) Benati, L.; Calestani, G.; Leardini, R.; Minozzi, M.; Nanni, D.; Spagnolo, P.; Strazzari, S.; Zanardi, G. J. Org. Chem., 2003, 68, 3454.
-
(2003)
J. Org. Chem
, vol.68
, pp. 3454
-
-
Benati, L.1
Calestani, G.2
Leardini, R.3
Minozzi, M.4
Nanni, D.5
Spagnolo, P.6
Strazzari, S.7
Zanardi, G.8
-
135
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85196432966
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In these reactions even α-fragmentation with loss of a sulfanyl radical does not seem a drawback, since isonitriles and disulfides were only detected in few cases and just in trace amounts
-
In these reactions even α-fragmentation with loss of a sulfanyl radical does not seem a drawback, since isonitriles and disulfides were only detected in few cases and just in trace amounts.
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