Novel 1,3-dipolar cycloaddition reaction of carbonyl ylide with o- quinones

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5627-5630

  Nair, Vijay ^a   Sheela, K C ^a   Radhakrishnan, K V ^a   Rath, Nigam P ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; X RAY ANALYSIS;

EID: 0032581629     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01065-X     Document Type: Article

References (20)

1. 1. (a) Nair, V.; Kumar, S. Synlett 1996, 12, 1143 and references cited therein.
2. (b) Nair, V.; Kumar, S.; Rath, N. P.; Morton, G. O. Chem. Lett. 1995, 383.
3. (c) Nair, V.; Kumar, S.; Anilkumar, G.; Nair, J. S. Tetrahedron 1995, 51, 9155.
4. (d) Nair, V.; Kumar, S. J. Chem. Soc., Perkin Trans. I 1996, 443.
5. e). Nair, V.; Kumar, S. Synth. Commun. 1996, 26, 217.
6. 2. For earlier work on the Diels -Alder reactions of o-quinones see, Patai, S.; Rappoport, Z. In The Chemistry of Quinonoid Compounds, Vol. 2, John Wiley & Sons, New York, 1988.
7. 3. Padwa, A. In 1,3-Dipolar Cycloaddition chemistry, Wiley-Interscience, New York, 1984.
8. 4. Kommissarova, N. L.; Belostotskaya, I. S.; Vol'eva, V. B.; Dzhuaryan, E. V.; Novikova I. A.; Ershov V. V. Izv.Akad. Nauk. SSSR, Ser.Khim (Eng. Trasl.) 1981, 2360.
9. 5 (a) Friedrichsen, W.; Schröer, W. D.; Debaerdemaeker, T. Justus Liebigs Ann. Chem. 1980, 1850;
10. (b) Friedrichsen, W.; Schröer, W. D.; Debaerdemaeker, T. Justus Liebigs Ann. Chem. 1980, 1836.
11. (c) Lawson, A.; Miles, D. H. J. Chem. Soc. 1959, 2865; Ibid 1960, 1945.
12. (c) Lawson, A.; Miles, D. H. J. Chem. Soc. 1959, 2865; Ibid 1960, 1945.
13. 6. (a) Friedrichsen, W.; Krüeger, C.; Kujath, E.; Liebezeit, G.; Mohr, S. Tetrahedron Lett. 1979, 237.
14. (b) Friedrichsen, W.; Schmidt, R.; van Hummel, G. J.; van den Ham, D. M. W. Ann. 1981, 521;
15. (c) Friedrichsen, W.; Kappe, T.; Böttcher, A. Heterocycles 1982, 19, 1083.
16. 7. Nair, V.; Radhakrishnan, K. V.; Nair, A. G.; Bhadbhade, M. M. Tetrahedron Lett. 1996, 37, 5623.
17. 8. Padwa, A.; Fryxel, G. E.; Zhi, L. J. Am.Chem. Soc. 1990, 112, 3100.
18. 9. Typical experimental procedure: 3,5-Di-tert-butyl-1,2-benzoquinone 3 (0.220 g,1 mmol) was added to a solution of 1-diazo-5-phenyl-2,5-pentanedione 1 (0.243 g, 1.2 mmol) and Rh(II)acetate (catalytic amount) in dry toluene (8 mL) at room temperature under argon atmosphere and stirred. When the reaction was complete (as indicated by TLC, 35 min.), the solvent was evaporated in vacuo. The residue obtained was purified using a chromatotron (silica gel, Merck, TLC grade, 7749). Elution with 1% ethyl acetate in hexane afforded 4 (0.297 g, 76%) as pale yellow crystalline solid (m.p 208-209 °C).
19. 3). δ 201.85, 199.33, 147.49, 144.75, 138.72, 133.69, 128.70, 128.20, 125.29, 122.54, 110.51, 87.90, 82.08, 35.67, 34.56, 33.26, 29.25, 28.38. CHN analysis: Found: C-75.61%, H-7.95%. (Calculated: C-76.11%, H-7.66%).
20. -1; Reflections collected = 20474. (Sheldrick, G. M., Siemens, Analytical X-ray Division, Madison, WI, 1995).