Generation of cyclohexyne and its diels-alder reaction with α-pyrones

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 3039-3040

  Atanes, Nieves ^a   Escudero, Sonia ^a   Pérez, Dolores ^a   Guitián, Enrique ^a   Castedo, Luis ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; CYCLOALKENE; CYCLOHEXENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR STABILITY; SYNTHESIS;

BETULACEAE;

EID: 0032492962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00328-1     Document Type: Article

References (12)

1. 1. (a) Hoffmann, R.W. Dehydrobenzene and Cycloalkynes, Academic Press: New York, 1967.
2. (b) Grundmann, C.; Houben-Weyl, Methoden der Organischen Chemie; Thieme Verlag: Stuttgart, 1981; Vol. 5, 2B, p. 615.
3. (c) Gilchrist, T. L.; in The Chemistry of Functional Groups, Suppl. C.: The Chemistry of Triple-Bonded Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1983; p. 383.
4. (d) Hart, H. in The Chemistry of Functional Groups, Suppl. C2.: The Chemistry of Triple-Bonded Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1984; p. 1017.
5. 2. Krebs, A.; Wilke, J. Angle Strained Cycloalkynes in Topics in Current Chemistry 1983, 109, 189.
6. 3. Over the last 20 years research into cycloalkyne chemistry has focused mainly on metal-cycloalkyne complexes, which has resulted in the preparation and characterization of stable cyclohexyne complexes with W, Co, Zr, Pt, Os and Ni. See Bennett, M. A.; Wenger, E. Chem. Ber./Recueil 1997, 130, 1029 and references therein.
7. 4. Olivella, S.; Pericás, M. A. ; Riera, A; Solé, A. J. Org. Chem. 1987, 52, 4160.
8. 5. Hitherto, the methods used to generate cycloalkynes, specially cyclohexyne, have been those used for the formation of benzyne. See references 1 and 2.
9. 6. See Shakespeare, W. C.; Johnson, R. P. J. Am. Chem. Soc. 1990, 112, 8578 and references therein.
10. 7. A similar procedure has been used to generate of 1,2,3-cyclohexatriene in ref. 6.
11. 8. Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Tetrahedron Lett. 1997, 38, 5375.
12. 9. All new compounds show correct spectroscopic data.