Electro-organic reactions. Part 46. Diels-Alder trapping of o-quinodimethane generated by redox-mediated cathodic reduction of α,α′-dibromo-o-xylene in the presence of hindered dienophiles

Tetrahedron

Volumn 52, Issue 22, 1996, Pages 7771-7778

  Oguntoye, Erada ^a   Szunerits, Sabine ^a   Utley, James H P ^a   Wyatt, Peter B ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BETULACEAE;

2 QUINDIMETHANE; ALKENE; ALPHA,ALPHA' DIBROMO 2 XYLENE; ANION; BENZOQUINONE DERIVATIVE; MALEIC ANHYDRIDE; MALEIMIDE DERIVATIVE; METHANE; ORTHO XYLENE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIC POTENTIOMETRY; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

EID: 0030006886     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00345-6     Document Type: Article

References (17)

1. For part 45 see Utley, J. H. P.; Güllü, M.; De Matteis, C. I.; Motevalli, M.; Nielsen, M. F. Tetrahedron, 1995, 57, 11873.
2. Eru, E.; Hawkes, G. E.; Utley, J. H. P.; Wyatt, P. B. Tetrahedron 1995, 51, 3033.
3. Bartlett, P. D.; Blakeney, A. J.; Kimura, M.; Watson, W. H. J. Am. Chem. Soc. 1980, 102, 1383.
4. Smith, W. B.; Shoulders, B. A. J. Phys. Chem. 1965, 69, 2022; Diels, O.; Alder, K. Liebigs Ann. Chem. 1931, 191.
5. Smith, W. B.; Shoulders, B. A. J. Phys. Chem. 1965, 69, 2022; Diels, O.; Alder, K. Liebigs Ann. Chem. 1931, 191.
6. Bartlett, P. D.; Ryan, M. J.; Cohen, S. G. J. Am. Chem. Soc. 1942, 64, 2649.
7. Hurd, C. D.; Juel, L. H. J. Am. Chem. Soc. 1955, 77, 601.
8. Hart, H.; Shamouilian, S.; Takehira, Y. K. J. Org. Chem. 1981, 46, 4427.
9. Chaturvedi, J.; Verma, S. M. Indian J. Chem., Sect B 1990, 29, 9.
10. Gualtieri, F.; Melchiorre, C.; Giannella, M.; Pigini, M. J. Org. Chem. 1975, 40, 2241.
11. We chose to study these compounds because selective allylation of 2-methylcyclopentane-1,3-dione at C-2 is easily performed; hydrogenation then gives 2-methyl-2-propylcyclopentane-1,3-dione. The analogous 2,2-dimethyl-compounds are known, but are less accessible because C-2 methylation of 2-methylcyclopentane-1,3-dione tends to give only moderate yields (see e.g. reference 11).
12. Agosta, W. C.; Smith, A. B. J. Org. Chem. 1970, 35, 3857.
13. Ronndan, N. G.; Paddon-Row, M. N.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2436; Huisgen, R.; Ooms, P. H. J.; Mingin, M.; Allinger, N. L. J. Am. Chem. Soc. 1980, 102, 3951.
14. Ronndan, N. G.; Paddon-Row, M. N.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2436; Huisgen, R.; Ooms, P. H. J.; Mingin, M.; Allinger, N. L. J. Am. Chem. Soc. 1980, 102, 3951.
15. Han, B. H.; Boudjouk, P. J. Org. Chem. 1982, 47, 751.
16. Chaturvedi, J.; Verma, S. M. Indian J. Chem., Sect B 1986, 25, 1083.
17. Agosta, W. C.; Smith, A. B. Chem. Commun. 1970, 685.