메뉴 건너뛰기




Volumn 73, Issue 6, 2008, Pages 2114-2121

Neighboring group participation in the additions of iodonium and bromonium ions to N-alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes (n = 1,2)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BROMINE COMPOUNDS; NITROGEN; OLEFINS; X RAY ANALYSIS;

EID: 41849097100     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702153q     Document Type: Article
Times cited : (12)

References (44)
  • 10
    • 33744889029 scopus 로고    scopus 로고
    • 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.
    • (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.
  • 11
    • 0021907215 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 15
    • 0029123806 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 17
    • 0029146331 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 22
    • 37049112822 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 24
    • 0000765122 scopus 로고    scopus 로고
    • For a related N-O-tosyl structure, see: Bussmann, R.; Heesing, A. Tetrahedron Lett. 1986, 27, 561-564.
    • (c) For a related N-O-tosyl structure, see: Bussmann, R.; Heesing, A. Tetrahedron Lett. 1986, 27, 561-564.
  • 25
    • 3543020909 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 28
    • 41849088760 scopus 로고    scopus 로고
    • Patent WO 00/75140 AI, 2000
    • (d) Mitch, C. H.; Quimby, S. J. Patent WO 00/75140 AI, 2000.
    • Mitch, C.H.1    Quimby, S.J.2
  • 29
    • 0342364958 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 30
    • 41849105698 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 33
    • 41849094390 scopus 로고    scopus 로고
    • 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
    • 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.
  • 34
    • 41849135809 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 37
    • 41849116973 scopus 로고
    • Those reactions are favored which involve the least change in atomic position and electronic configuration
    • 4th ed, John Wiley & Sons: New York
    • March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; p 782. "Those reactions are favored which involve the least change in atomic position and electronic configuration."
    • (1992) Advanced Organic Chemistry , pp. 782
    • March, J.1
  • 38
    • 4544346662 scopus 로고    scopus 로고
    • 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
    • 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.
  • 40
    • 85127160112 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 41
    • 0007699239 scopus 로고    scopus 로고
    • 5 distal from nitrogen. Krow, G.; Rodebaugh, R.; Grippi, M.; Carmosin, R. Synth. Commun. 1972, 2, 211-214.
    • 5 distal from nitrogen. Krow, G.; Rodebaugh, R.; Grippi, M.; Carmosin, R. Synth. Commun. 1972, 2, 211-214.
  • 42
    • 41849092131 scopus 로고    scopus 로고
    • 5-I. (Chemical Equation Presented)
    • 5-I. (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.