Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo [3,2,1]oct-3-en-2-one

Tetrahedron

Volumn 53, Issue 27, 1997, Pages 9313-9322

  Zaballos García, Elena ^a   González Rosende, M Eugenia ^a   Jorda Gregori, J Miquel ^a   Sepúlveda Arques, José ^a   Jennings, W Brian ^b   O'Leary, Donal ^b   Twomey, Suzanne ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

FURFURAL; HETEROCYCLIC COMPOUND; HYDRAZINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE;

EID: 0343487809     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00585-1     Document Type: Article

References (12)

1. González-Rosende, M.E.; Lozano-Lucia, O; Zaballos-Garcia; E. Sepúlveda-Arques, J. J. Chem. Res., 1995, (S) 260.
2. Alder, K.; T. Noble, T. Ber. Dtsch. Chem. Ges., 1943, 54; Huisgen, R.; Jacob, F. Liebigs Ann. Chem., 1954, 590, 37.
3. Alder, K.; T. Noble, T. Ber. Dtsch. Chem. Ges., 1943, 54; Huisgen, R.; Jacob, F. Liebigs Ann. Chem., 1954, 590, 37.
4. Jones, R.A.; Aznar Saliente, T.; Sepúlveda-Arques, J. J. Chem. Soc., Perkin Trans. I, 1984, 2541.
5. Sternhell, S.; Quart. Rev., 1969, 23, 236.
6. Kitahara, Y.; Murata, I.; Nitta, T. Tetrahedron Lett. 1967, 3003.
7. Gregory, B.; Hinz, W.; Jones, R.A.; Sepúlveda-Arques, J. J. Chem. Res., 1984, (M) 2801, (S) 311.
8. Okazawa, N.; Sorensen, T.S. Can. J. Chem. 1978, 56, 2737.
9. For reviews of hydrazide stereodynamics see, Nelsen, S.F. in Acyclic Organonitrogen Stereodynamics; Lambert, J.B.; Takeuchi, Y., Eds.; VCH, New York, 1992, ch. 3; Sutherland, I.O. Ann. Rep. NMR Spectrosc., 1971, 4, 71.
10. For reviews of hydrazide stereodynamics see, Nelsen, S.F. in Acyclic Organonitrogen Stereodynamics; Lambert, J.B.; Takeuchi, Y., Eds.; VCH, New York, 1992, ch. 3; Sutherland, I.O. Ann. Rep. NMR Spectrosc., 1971, 4, 71.
11. Anderson, J.E.; Lehn, J.M. Tetrahedron, 1968, 24, 123.
12. Burdon, J.; Hotchkiss, J.C.; Jennings, W.B. J. Chem. Soc., Perkin Trans. 2, 1976, 1052.