Photodimerization of N-acetyl-2-azetine: Synthesis of syn- diazatricyclooctane and anti-diazatricyclooctane (diaza-3-ladderane)

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5481-5484

  Dave, Paritosh R ^a   Duddu, Rajagopal ^a   Li, Jianchang ^a   Surapaneni, Rao ^b   Gilardi, Richard ^c  

^a SCIENCE APPLICATIONS INTERNATIONAL CORPORATION   (United States)

^b US Army ARDEC   (United States)

^c NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

N ACETYL 2 AZETINE; UNCLASSIFIED DRUG;

ARTICLE; DIMERIZATION; PHOTOCHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032581655     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01138-1     Document Type: Article

References (14)

1. 1. For reviews on photochemistry of enamides see: Campbell, A.I.; Lenz, G.R. Synthesis 1987, 421; Lenz, G.R. Synthesis 1978, 489.
2. 1. For reviews on photochemistry of enamides see: Campbell, A.I.; Lenz, G.R. Synthesis 1987, 421; Lenz, G.R. Synthesis 1978, 489.
3. 2. de Faria, A.R.; Matos, C.R.R.; Correia, C.R.D. Tet. Lett. 1993, 34, 27.
4. 3. For example: Steffan, G.; Schenck, G.O. Chem. Ber. 1967, 100, 3691; Whitney, R.A. Tet. Lett. 1981, 22, 2063; Whitney, R.A. Can. J. Chem. 1983, 61, 1158.
5. 3. For example: Steffan, G.; Schenck, G.O. Chem. Ber. 1967, 100, 3691; Whitney, R.A. Tet. Lett. 1981, 22, 2063; Whitney, R.A. Can. J. Chem. 1983, 61, 1158.
6. 3. For example: Steffan, G.; Schenck, G.O. Chem. Ber. 1967, 100, 3691; Whitney, R.A. Tet. Lett. 1981, 22, 2063; Whitney, R.A. Can. J. Chem. 1983, 61, 1158.
7. 4. The only example of an intramolecular enamide dimerization we found :Nakamura, Y.; Zsindely, J.; Schmid, H. Heterocycles 1976, 5, 427.
8. 5. For example: Warrener, R.N.; Ketschmer, G.; Paddon-row, M.N. J. Chem. Soc. Chem. Comm. 1977, 806; Marchand, A.P.; Duddu, R.; Bott, S.G.; Archibald, T. J. Org. Chem. 1994, 59, 1608.
9. 5. For example: Warrener, R.N.; Ketschmer, G.; Paddon-row, M.N. J. Chem. Soc. Chem. Comm. 1977, 806; Marchand, A.P.; Duddu, R.; Bott, S.G.; Archibald, T. J. Org. Chem. 1994, 59, 1608.
10. 6. Jung, M.E.; Choi, Y.M. J. Org. Chem. 1991, 56, 6729.
11. 7. Dave, P.R. J. Org. Chem. 1996, 61, 5453.
12. 8. Gaertner, V.R. J. Org. Chem. 1967, 32, 2972.
13. 9. Fleming, I. In Frontier Orbitals in Organic Chemical Reactions, Chapter 6, John Wiley and Sons, 1976.
14. 6): 3.33-3.43 (m, 2H), 4.71-4.82 (m, 2H), 5.0-5.08 (m, 2H), 5.32 (m, 2H).