In-line proximity effects in extended 7-azanorbornanes. 1. a new concept for modifying effector group separation based on the control of N-invertomer geometry

Organic Letters

Volumn 2, Issue 6, 2000, Pages 721-724

  Butler, Douglas N ^a   Hammond, Malcom L A ^a   Johnston, Martin R ^a   Sun, Guangxing ^a   Malpass, John R ^b   Fawcett, John ^b   Warrener, Ronald N ^a  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001178805     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9910969     Document Type: Article

References (18)

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10. Malpass, J. R.; Sun, G.; Fawcett, J.; Warrener, R. N. Tetrahedron Lett. 1998, 39, 3038-3086.
11. 10
12. We describe the particular [3]polynorbornanes using a three-letter prefix as a shorthand notation to designate the bridges (see Scheme 1 for the one-letter abbreviations for each bridge type), i.e., CNC[3]poly norbornane refers to the symmetrical product 24 in which the aza bridge is flanked by methylene bridges, whereas the ONπ[3]polynorbornane indicates an unsymmetrical product 14 in which the aza bridge is flanked by an oxygen bridge on one side and a 7-isopropylidene group on the other. For the bent isomers 27-33, the bent bridge is designated in parentheses, e.g., the CN(N) adduct 32 has the carbon and the N-benzyl bridge syn-related and the second NZ bridge on the underside of the [3]polynorbornane.
13. Malpass, J. R.; Butler, D. N.; Johnston, M. R.; Hammond, M. L. A.; Warrener, R. N. Org. Lett 2000, 2, 725-728.
14. 1H NMR δ 0.87 (2H, d, J = 8.1 Hz), 1.71 (4H, s), 2.56 (4H, s), 2.61 (4H, s), 3.12 (2H, d, J = 8.1 Hz), 3.74 (12H), 3.76 (4H, s), 5.08 (4H, s), 6.07 (4H, s), 7.15-7.40 (10H, m).
15. Butler, D. N.; Malpass, J. R.; Margetic, D.; Russell, R. A.; Sun, G.; Warrener, R. N. Synlett 1998, 588-589.
16. Warrener, R. N.; Hammond, M. L. A.; Butler, D. N. 1999, unpublished results.
17. 15N NMR spectroscopy, and this aspect will be discussed elsewhere.
18. Warrener, R. N.; Margetic, D.; Sun, G.; Amarasekara, A. S.; Foley, P.; Butler, D. N.; Russell, R. A. Tetrahedron Lett. 1999, 40, 4111-4114.