Trapping enols of esters and lactones with diazomethane

Tetrahedron Letters

Volumn 48, Issue 13, 2007, Pages 2245-2249

  Morales Ríos, Martha S ^a   López Camacho, Perla Y ^a   Suárez Castillo, Oscar R ^b   Joseph Nathan, Pedro ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DEL ESTADO DE HIDALGO   (Mexico)

Author keywords

Dicarbonylfuroindoles; Diazomethane; Enols of esters; Enols of lactones; Ketene O,O dialkyl acetals

Indexed keywords

ACETAL DERIVATIVE; ALKYL GROUP; CARBONYL DERIVATIVE; DIAZOMETHANE; ESTER DERIVATIVE; INDOLE DERIVATIVE; KETENE DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOISOMERISM; STEREOSPECIFICITY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 33847289365     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.006     Document Type: Article

References (35)

1. For reviews on carboxylic acid enols, see:. Hegarty A.F., and O'Neill P. In: Rappoport Z. (Ed). The Chemistry of Enols (1990), Wiley, Chichester Chapter 10, p 639
2. Kresge A.J. Chem. Soc. Rev. 25 (1996) 275-280
3. Andraos J., Chiang Y., Kresge A.J., and Popik V.V. J. Am. Chem. Soc. 119 (1997) 8417-8424
4. Carrondo M.A.A.F.d.C.T., Matias P.M., Heggie W., and Page P.R. Struct. Chem. 5 (1994) 73-77
5. Glatz B., Helmchen G., Muxfeldt H., Porcher H., Prewo R., Senn J., Stezowski J.J., Stojda R.J., and White D.R. J. Am. Chem. Soc. 101 (1979) 2171-2181
6. Mukhopadhyaya J.K., Sklenák S., and Rappoport Z. J. Am. Chem. Soc. 122 (2000) 1325-1336
7. O'Neill P., and Hegarty A.F. J. Chem. Soc., Chem. Commun. (1987) 744-745
8. Yamataka H., and Rappoport Z. J. Am. Chem. Soc. 122 (2000) 9818-9828
9. Perrin C.L., and Nielson J.B. Annu. Rev. Phys. Chem. 48 (1997) 511-544
10. Gao J. J. Mol. Struct. (THEOCHEM) 370 (1996) 203-208
11. Rosenberg R.E. J. Org. Chem. 63 (1998) 5562-5567
12. Raspoet G., Nguyen M.T., Kelly S., and Hegarty A.F. J. Org. Chem. 63 (1998) 9669-9677
13. Sung K., and Tidwell T.T. J. Am. Chem. Soc. 120 (1998) 3043-3048
14. Nguyen M.T., Sengupta D., Raspoet G., and Vanquickenborne L.G. J. Phys. Chem. 99 (1995) 11883-11888
15. Skancke P.N. J. Phys. Chem. 96 (1992) 8065-8069
16. Duan X., and Page M. J. Am. Chem. Soc. 117 (1995) 5114-5119
17. Sklenak S., Apeloig Y., and Rappoport Z. J. Am. Chem. Soc. 120 (1998) 10359-10364
18. Lei Y.X., Cerioni G., and Rappoport Z. J. Org. Chem. 65 (2000) 4028-4038
19. Allen B.M., Hegarty A.F., and O'Neill P. J. Chem. Soc., Perkin Trans. 2 (1997) 2733-2736
20. Vilsmaier E., Joerg K., and Mass G. Chem. Ber. 117 (1984) 2947-2962
21. Bruce M.I., Walton J.K., Williams M.L., Skelton B.W., and White A.H. J. Organomet. Chem. 212 (1981) C35-C38
22. Bruce M.I., Walton J.K., Williams M.L., Hall S.R., Skelton B.W., and White A.H. J. Chem. Soc., Dalton Trans. (1982) 2209-2220
23. Morales-Ríos M.S., Rivera-Becerril E., and Joseph-Nathan P. Tetrahedron: Asymmetry 16 (2005) 2493-2499
24. Morales-Ríos M.S., Suárez-Castillo O.R., Trujillo-Serrato J.J., and Joseph-Nathan P. J. Org. Chem. 66 (2001) 1186-1192
25. Morales-Ríos M.S., Suárez-Castillo O.R., and Joseph-Nathan P. J. Chem. Soc., Perkin Trans. 2 (2000) 769-775
26. Morales-Ríos M.S., Santos-Sánchez N.F., Fragoso-Vázquez M.J., Alagille D., Villagómez-Ibarra J.R., and Joseph-Nathan P. Tetrahedron 59 (2003) 2843-2853
27. Eberlin A.R., and Williams D.L.H. J. Chem. Soc., Perkin Trans. 2 (1996) 883-887 1043-1046
28. Lei Y.X., and Rappoport Z. J. Org. Chem. 67 (2002) 6971-6978
29. Yamataka H., and Rappoport Z. J. Am. Chem. Soc. 122 (2000) 9818-9828
30. Taskinen E., Salmela J., and Haapasaari K. Struct. Chem. 8 (1997) 425-433
31. +, 10), 336 (18), 304 (100)
32. 3. The CCDC deposition number is 635173.
33. Lei Y.X., Cerioni G., and Rappoport Z. J. Org. Chem. 66 (2001) 8379-8394
34. Heileman M.J., and Moore H.W. Tetrahedron Lett. 39 (1998) 3643-3646
35. Arndt F. Org. Synth. Coll. Vol. 2 (1943) 165-167