-
2
-
-
2142808506
-
-
Thiocarboxylation towards carbon nucleophiles such as enolates (a, b), phosphorous ylides (c), and an acyllithium (d). (a) Demuynck, C.; Thullier, A. Bull. Soc. Chim. Fr. 1969, 2434.
-
(1969)
Bull. Soc. Chim. Fr.
, pp. 2434
-
-
Demuynck, C.1
Thullier, A.2
-
6
-
-
0001283330
-
-
Thiocarboxylation towards heteroatom nucleophiles such as alcoholates (a), phenolates (b), and amines (a). (a) Ferm, R. J. Chem. Rev. 1957, 57, 621.
-
(1957)
Chem. Rev.
, vol.57
, pp. 621
-
-
Ferm, R.J.1
-
7
-
-
0006672993
-
-
(b) Chanyshev, N. T.; Kalaschnikov, S. M.; Kuramshin, E. M.; Naimushin, A. I.; Imashev, U. B. Zh. Obshch. Khim. 1990, 60, 2568;
-
(1990)
Zh. Obshch. Khim.
, vol.60
, pp. 2568
-
-
Chanyshev, N.T.1
Kalaschnikov, S.M.2
Kuramshin, E.M.3
Naimushin, A.I.4
Imashev, U.B.5
-
8
-
-
39749105477
-
-
Chem. Abstr 1991, 115, 28833r.
-
(1991)
Chem. Abstr
, vol.115
-
-
-
9
-
-
84985598253
-
-
For a high-yield synthesis of SeCO under mild conditions, see: Kondo, K.; Yokoyama, S.; Miyoshi, N.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1979, 18, 691.
-
(1979)
Angew. Chem., Int. Ed. Engl.
, vol.18
, pp. 691
-
-
Kondo, K.1
Yokoyama, S.2
Miyoshi, N.3
Murai, S.4
Sonoda, N.5
-
10
-
-
84985521959
-
-
Kondo, K.; Yokoyama, S.; Miyoshi, N.; Murai, S.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1979, 18, 692.
-
(1979)
Angew. Chem., Int. Ed. Engl.
, vol.18
, pp. 692
-
-
Kondo, K.1
Yokoyama, S.2
Miyoshi, N.3
Murai, S.4
Sonoda, N.5
-
11
-
-
61849087291
-
-
note
-
16 react at the sulfur atom.
-
-
-
-
16
-
-
0000208275
-
-
(e) Ohno, A.; Nakamura, K.; Shizume, Y.; Oka, S. Bull. Chem. Soc. Jpn. 1977, 50, 1003.
-
(1977)
Bull. Chem. Soc. Jpn.
, vol.50
, pp. 1003
-
-
Ohno, A.1
Nakamura, K.2
Shizume, Y.3
Oka, S.4
-
17
-
-
0001380070
-
-
(f) Masson, J.; Metzner, P.; Vialle, J. Tetrahedron 1977, 33, 3089.
-
(1977)
Tetrahedron
, vol.33
, pp. 3089
-
-
Masson, J.1
Metzner, P.2
Vialle, J.3
-
20
-
-
0000234180
-
-
(b) Okazaki, R.; Fukuda, N.; Oyama, H.; Inamoto, N. Chem. Lett. 1984, 101.
-
(1984)
Chem. Lett.
, pp. 101
-
-
Okazaki, R.1
Fukuda, N.2
Oyama, H.3
Inamoto, N.4
-
21
-
-
0000984998
-
-
(c) Vedejs, E.; Perry, D. A.; Wilde, R. G. J. Am. Chem. Soc. 1986, 108, 2985.
-
(1986)
J. Am. Chem. Soc.
, vol.108
, pp. 2985
-
-
Vedejs, E.1
Perry, D.A.2
Wilde, R.G.3
-
22
-
-
0001922323
-
-
Reactions of dithioesters with organolithium and Grignard reagents proceed in a thiophilic manner: (a) Léger, L.; Saquet, M. Bull. Soc. Chim. Fr. 1975, 657.
-
(1975)
Bull. Soc. Chim. Fr.
, pp. 657
-
-
Léger, L.1
Saquet, M.2
-
27
-
-
0001731372
-
-
(f) Bulpin, A. B., Masson, S.; Sene, A. Tetrahedron Lett. 1989, 30, 3415.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 3415
-
-
Bulpin, A.B.1
Masson, S.2
Sene, A.3
-
28
-
-
0000202984
-
-
Reactions of dithioesters with allyl, benzyl, propagyl, and vinyl Grignard reagents proceed in a carbophilic manner: (g) Masson, S.; Saquet, M.; Thuillier, A. Tetrahedron 1977, 33, 2949.
-
(1977)
Tetrahedron
, vol.33
, pp. 2949
-
-
Masson, S.1
Saquet, M.2
Thuillier, A.3
-
29
-
-
0001659101
-
-
(h) Gosselin, P.; Masson, S.; Thuillier, A. J. Org. Chem. 1979, 44, 2807.
-
(1979)
J. Org. Chem.
, vol.44
, pp. 2807
-
-
Gosselin, P.1
Masson, S.2
Thuillier, A.3
-
30
-
-
0011721511
-
-
Diorganocuprates react with dithioesters at the carbon atom: (i) Bertz, S. H.; Dabbagh, G.; Williams, L. M. J. Org. Chem. 1985, 50, 4414.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 4414
-
-
Bertz, S.H.1
Dabbagh, G.2
Williams, L.M.3
-
31
-
-
61849179675
-
-
(a) Beak, P.; Yamamoto, J.; Upton, C. J. J. Org. Chem. 1975, 40, 305.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 305
-
-
Beak, P.1
Yamamoto, J.2
Upton, C.J.3
-
32
-
-
84980167331
-
-
(b) Walter, W.; Lüke, H.-W. Angew. Chem., Int. Ed. Engl. 1977, 16, 535.
-
(1977)
Angew. Chem., Int. Ed. Engl.
, vol.16
, pp. 535
-
-
Walter, W.1
Lüke, H.-W.2
-
33
-
-
0011722889
-
-
(c) Karakasa, T.; Hanzawa, T.; Motoki, S. Bull. Chem. Soc. Jpn. 1979, 52, 3469.
-
(1979)
Bull. Chem. Soc. Jpn.
, vol.52
, pp. 3469
-
-
Karakasa, T.1
Hanzawa, T.2
Motoki, S.3
-
34
-
-
0001117777
-
-
(d) Tominaga, Y.; Kohra, S.; Hosomi, A. Tetrahedron Lett. 1987, 28, 1529.
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 1529
-
-
Tominaga, Y.1
Kohra, S.2
Hosomi, A.3
-
35
-
-
84981782970
-
-
(a) Walter, W.; Bode, K.-D. Angew. Chem., Int. Ed. Engl. 1966, 5, 447.
-
(1966)
Angew. Chem., Int. Ed. Engl.
, vol.5
, pp. 447
-
-
Walter, W.1
Bode, K.-D.2
-
40
-
-
0021239777
-
-
(f) Kelly, T. R.; Echavarren, A.; Chandrakumar, N. S.; Köksal, Y. Tetrahedron Lett. 1984, 25, 2127.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 2127
-
-
Kelly, T.R.1
Echavarren, A.2
Chandrakumar, N.S.3
Köksal, Y.4
-
44
-
-
0001770848
-
-
(b) Meijer, J.; Ruitenberg, K.; Westmijze, H.; Vermeer, P. Synthesis 1981, 551.
-
(1981)
Synthesis
, pp. 551
-
-
Meijer, J.1
Ruitenberg, K.2
Westmijze, H.3
Vermeer, P.4
-
48
-
-
37049097696
-
-
Only one example of thiophilic attack: (f) Okazaki, R.; Fujii, T.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1984, 1010.
-
(1984)
J. Chem. Soc., Chem. Commun.
, pp. 1010
-
-
Okazaki, R.1
Fujii, T.2
Inamoto, N.3
-
49
-
-
37049094819
-
-
(a) Narasimhan, L.; Sanitra, R.; Swenton, J. S. J. Chem. Soc., Chem. Commun. 1978, 719.
-
(1978)
J. Chem. Soc., Chem. Commun.
, pp. 719
-
-
Narasimhan, L.1
Sanitra, R.2
Swenton, J.S.3
-
50
-
-
0000587954
-
-
(b) Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Veale, C. A.; Furst, G. T. J. Am. Chem. Soc. 1987, 109, 2504.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 2504
-
-
Nicolaou, K.C.1
McGarry, D.G.2
Somers, P.K.3
Veale, C.A.4
Furst, G.T.5
-
55
-
-
37049068276
-
-
(a) Barbaro, G.; Battaglia, A.; Giorgianni, P.; Maccagnani, G.; Macciantelli, D. J. Chem. Soc., Perkin Trans. 1 1986, 381.
-
(1986)
J. Chem. Soc., Perkin Trans. 1
, pp. 381
-
-
Barbaro, G.1
Battaglia, A.2
Giorgianni, P.3
Maccagnani, G.4
Macciantelli, D.5
-
56
-
-
0001267279
-
-
(b) Bonini, B. F.; Maccagnani, G.; Masiero, S.; Mazzanti, G.; Zani, P. Tetrahedron Lett. 1989, 30, 2677.
-
(1989)
Tetrahedron Lett.
, vol.30
, pp. 2677
-
-
Bonini, B.F.1
Maccagnani, G.2
Masiero, S.3
Mazzanti, G.4
Zani, P.5
-
57
-
-
61849148853
-
-
note
-
23
-
-
-
-
58
-
-
0011767449
-
-
(a) Okazaki, R.; Ishii, A.; Inamoto, N. Tetrahedron Lett. 1984, 25, 5147.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 5147
-
-
Okazaki, R.1
Ishii, A.2
Inamoto, N.3
-
59
-
-
0000393401
-
-
(b) Guziec, F. S., Jr.; SanFilippo, L. J.; Murphy, C. J.; Moustakis, C. A.; Cullen, E. R. Tetrahedron 1985, 41, 4843.
-
(1985)
Tetrahedron
, vol.41
, pp. 4843
-
-
Guziec Jr., F.S.1
SanFilippo, L.J.2
Murphy, C.J.3
Moustakis, C.A.4
Cullen, E.R.5
-
60
-
-
0000752548
-
-
(c) Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1988, 61, 861.
-
(1988)
Bull. Chem. Soc. Jpn.
, vol.61
, pp. 861
-
-
Ishii, A.1
Okazaki, R.2
Inamoto, N.3
-
61
-
-
33845184037
-
-
Okazaki, R.; Kumon, N.; Inamoto, N. J. Am. Chem. Soc. 1989, 111, 5949.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 5949
-
-
Okazaki, R.1
Kumon, N.2
Inamoto, N.3
-
62
-
-
0011776819
-
-
(a) Okazaki, R.; Ishii, A.; Inamoto, N. J. Chem. Soc., Chem. Commun. 1986, 71.
-
(1986)
J. Chem. Soc., Chem. Commun.
, pp. 71
-
-
Okazaki, R.1
Ishii, A.2
Inamoto, N.3
-
63
-
-
0011752612
-
-
(b) Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1986, 59, 2529.
-
(1986)
Bull. Chem. Soc. Jpn.
, vol.59
, pp. 2529
-
-
Ishii, A.1
Okazaki, R.2
Inamoto, N.3
-
64
-
-
0030576892
-
-
Maeda, H.; Kambe, N.; Sonoda, N.; Fujiwara, S.; Shin-ike, T. Tetrahedron 1996, 52, 12165.
-
(1996)
Tetrahedron
, vol.52
, pp. 12165
-
-
Maeda, H.1
Kambe, N.2
Sonoda, N.3
Fujiwara, S.4
Shin-ike, T.5
-
65
-
-
0000251192
-
-
Sekiguchi, M.; Ogawa, A.; Fujiwara, S.; Ryu, I.; Kambe, N.; Sonoda, N. Chem. Lett. 1990, 2053.
-
(1990)
Chem. Lett.
, pp. 2053
-
-
Sekiguchi, M.1
Ogawa, A.2
Fujiwara, S.3
Ryu, I.4
Kambe, N.5
Sonoda, N.6
-
67
-
-
61849116809
-
-
note
-
The reaction of SCO with PhLi was examined in detail in order to compare the reactivities of SeCO and SCO. Thus, SCO was treated with PhLi under identical conditions as in run 1 of Table 1 by using MeI instead of BzBr; the corresponding thiol ester 3 was obtained in 95% yield via carbophilic attack without any thiophilic products (eq (Formula Presented)
-
-
-
-
68
-
-
0000885719
-
-
Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355 and 4359.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 4355
-
-
Sviridov, A.F.1
Ermolenko, M.S.2
Yashunsky, D.V.3
Kochetkov, N.K.4
-
69
-
-
61849102397
-
-
note
-
It is not clear yet why organocopper reagents prefer carbophilic attack to selenophilic attack.
-
-
-
-
70
-
-
0001729405
-
-
Trost, B. M., Fleming, I., Eds; Pergamon Press: Oxford
-
For recent reviews, see: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: Oxford, 1991; Vol. 6, pp 461-484.
-
(1991)
Comprehensive Organic Synthesis
, vol.6
, pp. 461-484
-
-
Ogawa, A.1
Sonoda, N.2
-
71
-
-
0001611562
-
-
Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Pergamon Press: Oxford
-
(b) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Pergamon Press: Oxford, 1995; Vol. 5, pp 231-255.
-
(1995)
Comprehensive Organic Functional Group Transformations
, vol.5
, pp. 231-255
-
-
Ogawa, A.1
Sonoda, N.2
-
72
-
-
0029790019
-
-
(a) Maeda, H.; Fujiwara, S.; Shin-ike, T.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 8160.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 8160
-
-
Maeda, H.1
Fujiwara, S.2
Shin-ike, T.3
Kambe, N.4
Sonoda, N.5
-
73
-
-
0344616618
-
-
(b) Maeda, H.; Nishiyama, A.; Kambe, N.; Sonoda, N.; Fujiwara, S.; Shin-ike, T. Synthesis 1997, 342.
-
(1997)
Synthesis
, pp. 342
-
-
Maeda, H.1
Nishiyama, A.2
Kambe, N.3
Sonoda, N.4
Fujiwara, S.5
Shin-ike, T.6
-
74
-
-
61849149973
-
-
note
-
As for the hitherto known synthetic methods of selenol esters, see the literature cited in ref 28b.
-
-
-
-
76
-
-
0000536145
-
-
Nishiyama, Y.; Katsuura, A.; Negoro, A.; Hamanaka, S.; Miyoshi, N.; Yamana, Y.; Ogawa, A.; Sonoda, N. J. Org. Chem. 1991, 56, 3776.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 3776
-
-
Nishiyama, Y.1
Katsuura, A.2
Negoro, A.3
Hamanaka, S.4
Miyoshi, N.5
Yamana, Y.6
Ogawa, A.7
Sonoda, N.8
-
77
-
-
0000961482
-
-
Kojima, Y.; Ibi, K.; Kanda, T.; Ishihara, H.; Murai, T.; Kato, S. Bull. Chem. Soc. Jpn. 1993, 66, 990.
-
(1993)
Bull. Chem. Soc. Jpn.
, vol.66
, pp. 990
-
-
Kojima, Y.1
Ibi, K.2
Kanda, T.3
Ishihara, H.4
Murai, T.5
Kato, S.6
-
78
-
-
0000859086
-
-
Inoue, T.; Takeda, T.; Kambe, N.; Ogawa, A.; Ryu, I.; Sonoda, N. J. Org. Chem. 1994, 59, 5824.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 5824
-
-
Inoue, T.1
Takeda, T.2
Kambe, N.3
Ogawa, A.4
Ryu, I.5
Sonoda, N.6
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