Fused cyclobutenomaleimides: Reactive dienophiles for molrac construction

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3773-3776

  Warrener, Ronald N ^a   Maksimovic, Ljiljana ^a   Pitt, Ian G ^a,d   Mahadevan, Indu ^b   Russell, Richard A ^b   Tiekink, Edward R T ^c  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

^c UNIVERSITY OF ADELAIDE   (Australia)

^d Environment Protection Group   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON; SUCCINIMIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029992983     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00679-X     Document Type: Article

References (14)

1. Kumar, K.; Tepper, R. J.; Zeng, Y.; Zimmt, M. B. J. Org. Chem. 1995, 60, 4051-4066 and references therein.
2. Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Amer. Chem. Soc. 1994, 116, 3645-3646; Warrener, R. N.; Abbenante, G.; Solomon, R. G.; Russell, R. A. Tetrahedron Lett. 1994, 35, 7639-7642; Warrener, R. N.; Elsey, G. M.; Houghton, M. A. J. Chem. Soc., Chem. Commun. 1995, 1417-1418.
3. Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Amer. Chem. Soc. 1994, 116, 3645-3646; Warrener, R. N.; Abbenante, G.; Solomon, R. G.; Russell, R. A. Tetrahedron Lett. 1994, 35, 7639-7642; Warrener, R. N.; Elsey, G. M.; Houghton, M. A. J. Chem. Soc., Chem. Commun. 1995, 1417-1418.
4. Warrener, R. N.; Abbenante, G.; Kennard, C. H. L. J. Amer. Chem. Soc. 1994, 116, 3645-3646; Warrener, R. N.; Abbenante, G.; Solomon, R. G.; Russell, R. A. Tetrahedron Lett. 1994, 35, 7639-7642; Warrener, R. N.; Elsey, G. M.; Houghton, M. A. J. Chem. Soc., Chem. Commun. 1995, 1417-1418.
5. Lynn-Cobb, R.; Mahan, J.E. J. Org. Chem., 1977, 42, 1948-1951.
6. Warrener, R. N.; Elsey, G. M.; Pitt, I. G.; Russell, R. A. Aust. J. Chem. 1995, 48, 241-260.
7. Warrener, R. N.; Pitt, I. G.; Butler, D. N. J. Chem. Soc., Chem. Commun. 1983, 1340-1342.
8. One isomer of this mixture (presumably the one with the bromine substituents in the more accessible anti-fused site) debrominates faster than the other, but exact structures for these adducts have not been rigorously determined.
9. 9
10. Warrener, R. N.; Elsey, G. M.; Maksimovic, L.; Johnston, M.R.; Kennard, C. H. L. Tetrahedron Lett. 1995, 36, 7753-7756.
11. In this case the reaction was not stereospecific and a second isomeric product was obtained in 27% yield. This was not characterised.
12. 1H NMR chemical shifts of succinimide N-methyl groups
13. b protons. Scheme 5
14. Russell, R.A.; Longmore, R.W.; Weerasuria, K.D.V. Warrener, R.N. Aust. J. Chem., 1991, 44, 1341-1345.