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(c) For addition of bromine to an N-O-tosyl-2-azabicyclo[2.2.1] hept-5-ene without rearrangement, see: Biehler, J.-M.; Bleury, J.-P. Tetrahedron 1971, 27, 3171-3196.
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For addition of bromine reagents to related 2-azabicyclo[2.2.1]hept-5- ene-2-ones with rearrangement, see: (a) Faith, W. C.; Booth, C. A.; Foxman, B. M.; Snider, B. B. J. Org. Chem. 1985, 50, 1983-1985.
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For addition of molecular fluorine to related 2-azabicyclo[2.2.1]hept-5- ene-2-ones to give both rearranged and non-rearranged products, see: (a) Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron 1995, 51, 8783-8798.
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For addition of molecular fluorine to related 2-azabicyclo[2.2.1]hept-5- ene-2-ones to give both rearranged and non-rearranged products, see: (a) Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron 1995, 51, 8783-8798.
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For iodofluorination of related N-acylated-2-azabicyclo[2.2.1] hept-5-ene-2-ones to give unrearranged cis addition products, see: Toyota, A.; Ono, Y.; Kaneko, C. Tetrahedron Lett. 1995, 36, 6123-6126.
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For iodofluorination of related N-acylated-2-azabicyclo[2.2.1] hept-5-ene-2-ones to give unrearranged cis addition products, see: Toyota, A.; Ono, Y.; Kaneko, C. Tetrahedron Lett. 1995, 36, 6123-6126.
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37049112822
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For rearrangement of an N-tosyl-2-azabicyclo[2.2.2]hex-5-ene, see: (a) Holmes, A. B.; Raithby, P. R.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1983, 1490-1492.
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For rearrangement of an N-tosyl-2-azabicyclo[2.2.2]hex-5-ene, see: (a) Holmes, A. B.; Raithby, P. R.; Thompson, J.; Baxter, A. J. G.; Dixon, J. J. Chem. Soc., Chem. Commun. 1983, 1490-1492.
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23
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0025009420
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For rearrangement of a related epoxide, see
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(b) For rearrangement of a related epoxide, see: Holmes, A. B.; Kee, A.; Ladduwahetty, T.; Smith, D. F. J. Chem. Soc., Chem. Commun. 1990, 1412-1414.
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For a related N-O-tosyl structure, see: Bussmann, R.; Heesing, A. Tetrahedron Lett. 1986, 27, 561-564.
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(c) For a related N-O-tosyl structure, see: Bussmann, R.; Heesing, A. Tetrahedron Lett. 1986, 27, 561-564.
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25
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3543020909
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For rearrangement of N-alkyl-2-azabicyclo[2.2.1]hept-5-enes upon addition of bromine reagents, see: (a) Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334.
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For rearrangement of N-alkyl-2-azabicyclo[2.2.1]hept-5-enes upon addition of bromine reagents, see: (a) Malpass, J. R.; White, R. J. Org. Chem. 2004, 69, 5328-5334.
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For rearrangement of N-alkyl-2-azabicyclo[2.2.2]oct-5-enes upon addition of bromine reagents, see ref 7b and Hutchins, R. O.; Rua, L., Jr. J. Org. Chem. 1975, 40, 2567-2568.
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For rearrangement of N-alkyl-2-azabicyclo[2.2.2]oct-5-enes upon addition of bromine reagents, see ref 7b and Hutchins, R. O.; Rua, L., Jr. J. Org. Chem. 1975, 40, 2567-2568.
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30
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41849105698
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See ref 1c. N-Chlorosuccinimide and Selectfluor react with alkene 1 to give ring-opened 5-aminopenten-2-a1 by electrophilic attack of halonium ion on nitrogen.
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See ref 1c. N-Chlorosuccinimide and Selectfluor react with alkene 1 to give ring-opened 5-aminopenten-2-a1 by electrophilic attack of halonium ion on nitrogen.
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31
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2542546731
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III; Ramjit, H. G
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(b) Krow, G. R.: Lin, G.; Yu, F.; Sonnet, P. E. Org. Lett. 2003, 5, 2739-2741.
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33
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41849094390
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Throughout this paper, we have chosen to use synlanti nomenclature to identify the stereochemistry of substituents on the non-nitrogen-containing bridges. This is to avoid the use of exolendo nomenclature, confusing to those accustomed to naming the related all-carbon-bridged bicyclic structures. The bridge with the nitrogen heteroatom is always the main bridge of highest priority before the bridge with fewest members. Thus, all substituents anti to nitrogen are endo, even when pointed toward a methylene bridge. Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; John Wiley & Sons, Inc, New York, 1991; pp 49-50
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Throughout this paper, we have chosen to use synlanti nomenclature to identify the stereochemistry of substituents on the non-nitrogen-containing bridges. This is to avoid the use of exolendo nomenclature, confusing to those accustomed to naming the related all-carbon-bridged bicyclic structures. The bridge with the nitrogen heteroatom is always the main bridge of highest priority before the bridge with fewest members. Thus, all substituents anti to nitrogen are endo, even when pointed toward a methylene bridge. Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; John Wiley & Sons, Inc.: New York, 1991; pp 49-50.
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34
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41849135809
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The iodofluoride 29a has also been prepared from the iodoalcohol 31b. See the accompanying manuscript: Krow, G. R.; Gandla, D.; Guo, W.; Centafont, R. A.; Lin, G.; DeBrosse, C.; Sonnet, P. E.; Ross, C. W., III; Ramjit, H. G.; Cannon, K. C. J. Org. Chem. 2008, 73, 2122-2129.
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The iodofluoride 29a has also been prepared from the iodoalcohol 31b. See the accompanying manuscript: Krow, G. R.; Gandla, D.; Guo, W.; Centafont, R. A.; Lin, G.; DeBrosse, C.; Sonnet, P. E.; Ross, C. W., III; Ramjit, H. G.; Cannon, K. C. J. Org. Chem. 2008, 73, 2122-2129.
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41849116973
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38
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4544346662
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Unrearranged cis products have been observed for additions of IX (X, F, OH) to an azabicyclic lactam; see ref 5. For 1,2-cis additions of bromine to alkene facilitated by neighboring oxygen, see: (a) Menzek, A, Altundas, A, Coruh, U, Akbulut, N, Vazquez Lopez, E. M, Hokelek, T, Erdonmez, A, Chem. 2004, 1143-1148
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Unrearranged cis products have been observed for additions of IX (X = F, OH) to an azabicyclic lactam; see ref 5. For 1,2-cis additions of bromine to alkene facilitated by neighboring oxygen, see: (a) Menzek, A.; Altundas, A.; Coruh, U.; Akbulut, N.; Vazquez Lopez, E. M.; Hokelek, T.; Erdonmez, A. Eur. J. Org. Chem. 2004, 1143-1148.
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40
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85127160112
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For a 1,2-cis addition of bromine to alkene facilitated by a neighboring arene, see: (c) Dastan, A. J. Chem. Res. 2005, 608-612.
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For a 1,2-cis addition of bromine to alkene facilitated by a neighboring arene, see: (c) Dastan, A. J. Chem. Res. 2005, 608-612.
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41
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0007699239
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5 distal from nitrogen. Krow, G.; Rodebaugh, R.; Grippi, M.; Carmosin, R. Synth. Commun. 1972, 2, 211-214.
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5 distal from nitrogen. Krow, G.; Rodebaugh, R.; Grippi, M.; Carmosin, R. Synth. Commun. 1972, 2, 211-214.
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42
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41849092131
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5-I. (Chemical Equation Presented)
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5-I. (Chemical Equation Presented)
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43
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0030948144
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0001579423
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