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2
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0013465265
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(b) Karlsson, J. O.; Svensson, A.; Gronowitz, S. J. Org. Chem. 1984, 49, 2018.
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Karlsson, J.O.1
Svensson, A.2
Gronowitz, S.3
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4
-
-
0011132083
-
-
Hill, B.; De Vleeschauwer, M.; Houde, K.; Belley, M. Synlett 1998, 407.
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(1998)
Synlett
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Hill, B.1
De Vleeschauwer, M.2
Houde, K.3
Belley, M.4
-
5
-
-
13844281866
-
-
Hallberg, A.; Frejd, T.; Gronowitz, S. Chem. Scr. 1979, 13, 186.
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(1979)
Chem. Scr.
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, pp. 186
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-
Hallberg, A.1
Frejd, T.2
Gronowitz, S.3
-
6
-
-
49249151364
-
-
3I (2.3 mL) and copper (5.0 g) in pyridine (13 ml) at 130 °C for 24 h. See: Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 42, 4071; for a related procedure.
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(1979)
Tetrahedron Lett.
, vol.42
, pp. 4071
-
-
Kobayashi, Y.1
Yamamoto, K.2
Kumadaki, I.3
-
7
-
-
13844267086
-
-
note
-
20 to yield 5a.
-
-
-
-
8
-
-
0035826341
-
-
The reverse of this reaction, the synthesis of benzothiophenes from phenylacetylenes, has been reported by: (a) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651.
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(2001)
Org. Lett.
, vol.3
, pp. 651
-
-
Flynn, B.L.1
Verdier-Pinard, P.2
Hamel, E.3
-
11
-
-
13844281865
-
-
note
-
The first step was found to be rate limiting based on the following observations. 1) The FBW rearrangement was reported repeatedly to occur rapidly and at temperature below -20 °C. 2) We haven't been able to isolate any of the non-rearranged products from the intermediate 2,2-diaryl-1- fluorovinyllithium 8, even when the reaction was quenched at -78 °C (first entry in Table 1). 3) In most reactions where there is no diphenylacetylene produced, the major product isolated is the starting benzothiophene 7.
-
-
-
-
12
-
-
0033525478
-
-
For recent articles describing FBW rearrangements, see: (a) Creton, E.; Rezaeï, H.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1999, 40, 1899.
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(1999)
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, pp. 1899
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-
Creton, E.1
Rezaeï, H.2
Marek, I.3
Normant, J.F.4
-
13
-
-
0031883452
-
-
(b) Mouriès, V.; Waschbüsch, R.; Carran, J.; Savignac, P. Synthesis 1998, 271.
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(1998)
Synthesis
, pp. 271
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-
Mouriès, V.1
Waschbüsch, R.2
Carran, J.3
Savignac, P.4
-
14
-
-
0037458895
-
-
Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339.
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J. Org. Chem.
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, pp. 1339
-
-
Shi Shun, A.L.K.1
Chernick, E.T.2
Eisler, S.3
Tykwinski, R.R.4
-
17
-
-
84947151032
-
-
Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
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(1981)
Synth. Commun.
, vol.11
, pp. 513
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-
Miyaura, N.1
Yanagi, T.2
Suzuki, A.3
-
19
-
-
0346863387
-
-
Werner, L. H.; Schroeder, D. C.; Ricca, S. Jr. J. Am. Chem. Soc. 1957, 79, 1675.
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(1957)
J. Am. Chem. Soc.
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, pp. 1675
-
-
Werner, L.H.1
Schroeder, D.C.2
Ricca Jr., S.3
-
21
-
-
13844280600
-
-
note
-
8ClFS: C, 64.00; H, 3.07. Found: C, 64.45; H, 3.00.
-
-
-
-
22
-
-
0000916895
-
-
The structure of 11 was confirmed by 2D-NOE studies. This reaction was also described by: Mulvaney, J. E.; Gardlund, Z. G.; Gardlund, S. L. J. Am. Chem. Soc. 1963, 85, 3897.
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(1963)
J. Am. Chem. Soc.
, vol.85
, pp. 3897
-
-
Mulvaney, J.E.1
Gardlund, Z.G.2
Gardlund, S.L.3
-
23
-
-
13844276293
-
-
note
-
2-Chloro-3-phenylbenzothiophene was prepared in 64% yield from 9a by lithiation with BuLi at -78 °C followed by reaction with N-chlorosuccinimide.
-
-
-
-
24
-
-
13844257043
-
-
note
-
The same reaction with s-BuLi yielded only 3-phenylbenzothiophene 13.
-
-
-
-
25
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-
0001760023
-
-
Yoshida, S.; Fujii, M.; Aso, Y.; Otsubo, T.; Ogura, F. J. Org. Chem. 1994, 59, 3077.
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J. Org. Chem.
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, pp. 3077
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-
Yoshida, S.1
Fujii, M.2
Aso, Y.3
Otsubo, T.4
Ogura, F.5
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26
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0028963542
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-
Soderquist, J. A.; Matos, K.; Rane, A.; Ramos, J. Tetrahedron Lett. 1995, 36, 2401.
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(1995)
Tetrahedron Lett.
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-
Soderquist, J.A.1
Matos, K.2
Rane, A.3
Ramos, J.4
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