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1) Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis, Butterworths, London, 1987, 75-78.
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Tin in Organic Synthesis
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Pereyre, M.1
Quintard, J.-P.2
Rahm, A.3
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8
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0030955447
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6) Curran, D. P.; Diederichsen, U.; Palovich, M. J. Am. Chem. Soc. 1997, 119, 4797-4804.
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Curran, D.P.1
Diederichsen, U.2
Palovich, M.3
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9
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0029990596
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and references therein
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7) The fragmentation of alkoxy radicals has been used for the transfer of formyl groups, see : Jarreton, O.; Skrydstrup, T.; Beau, J. M. J. Chem. Soc., Chem. Commun. 1996, 1661-1662 and references therein.
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Jarreton, O.1
Skrydstrup, T.2
Beau, J.M.3
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10
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0004220870
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VCH Publishers Inc., Weinheim
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8) Nicolaou, K. C.; Sorensen, E. J. Classics in Total Synthesis, VCH Publishers Inc., Weinheim, 1996, 712-717.
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Nicolaou, K.C.1
Sorensen, E.J.2
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11
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0028826606
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9) Cyclizations of substituted 4-pentenyl-1-oxy radicals have been described recently, see : Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706-6716.
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Hartung, J.1
Gallou, F.2
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0042789931
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10) For a review, see : Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115.
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Dowd, P.1
Zhang, W.2
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13
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0010663226
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To the best of our knowledge, radical transesterifications involving alkoxy radicals have not been reported
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11) To the best of our knowledge, radical transesterifications involving alkoxy radicals have not been reported.
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15
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33751500481
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b) Otera, J.; Danh-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307-5311.
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Otera, J.1
Danh-oh, N.2
Nozaki, H.3
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16
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0010749589
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note
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5: C, 57.89, H, 7.07. Found: C, 57.87, H, 7.15.
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17
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0010746323
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note
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14) We can not yet completely rule away another minor pathway for 2, involving an O-ketyl radical, cyclizing in a 6-exo-trig mode followed by a bromide β-elimination.
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18
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0000030495
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15) In comparison, the reaction of tin hydride with the analogous vinyl acceptor shows 83% of 6-exo-trig cyclization, 5% of 7-endo-trig, and 12% of 1,5-H transfer. See : Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051-6059.
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J. Am. Chem. Soc.
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Curran, D.P.1
Shen, W.2
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19
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0000696586
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16) Stien, D.; Samy, R.; Nouguier, R.; Crich, D.; Bertrand, M. P. J. Org. Chem. 1997, 62, 275-286.
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Stien, D.1
Samy, R.2
Nouguier, R.3
Crich, D.4
Bertrand, M.P.5
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20
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0002234783
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17) 5-endo-trig cyclizations involving all-carbon systems are quite rare, see for instance : a) Julia, M.; Le Goffic, F. Bull. Soc. Chim. Fr. 1965, 1550-1555
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(1965)
Bull. Soc. Chim. Fr.
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Julia, M.1
Le Goffic, F.2
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21
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0028851974
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b) Yamamoto, Y.; Ohno, M.; Eguchi, S. J. Am. Chem. Soc. 1995, 117, 9653-9661
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Yamamoto, Y.1
Ohno, M.2
Eguchi, S.3
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22
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0010656925
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c) Schmaltz, H-G.; Siegel, S.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2083-2385.
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Schmaltz, H.-G.1
Siegel, S.2
Bats, J.W.3
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24
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0010708377
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note
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5: C, 56.07, H, 6.59. Found: C, 56.00, H, 6.65.
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25
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0000457447
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19) a) Nozaki, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041-1044.
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Nozaki, K.1
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Utimoto, K.3
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0001434093
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b) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143-147.
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Miura, K.1
Ichinose, Y.2
Nozaki, K.3
Fugami, K.4
Oshima, K.5
Utimoto, K.6
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27
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84981922371
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20) Brown, H. C.; Midland, M. M. Angew. Chem., Int. Ed. Engl. 1972, 11, 692-700.
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Brown, H.C.1
Midland, M.M.2
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