An improved synthesis of 4-methylene-2-cyclohexen- 1-one

Synthetic Communications

Volumn 24, Issue 2, 1994, Pages 197-203

  Jung, Michael E ^a   Ray le, Heather L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0028266768     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397919408013819     Document Type: Article

References (14)

1. UCLA McCoy Award recipient, 1991-92; UCLA Hanson-Dow Teaching Award recipient, 1992. To whom correspondence should be addressed.
2. National Science Foundation Fellow, 1989-92.
3. For example, see Genet, J.-P.; Ficini, J. Tetrahedron Lett. 1979, 1499 and references within.
4. Rickards, R. W.; Rodwell, J. L.; Schmalzl, K. J. J. Chem. Soc, Chem. Commun. 1977, 849.
5. Birch, A. J. J. Proc. Roy. Soc. New S. Wales 1949, 83, 245.
6. Iio, H.; Isobe, M.; Kawai, T.; Goto, T. Tetrahedron 1979, 35, 941.
7. Lemmens, J. M.; Thijs, L.; Zwanenburg, B. Tetrahedron 1984, 40, 3331.
8. Danishefsky, S.; Kitahara, T. J. Org. Chem. 1975, 40, 538.
9. Berkowitz, W. F.; Amarasekara, A. S.; Perumattam, J. J. J. Org. Chem. 1987, 52, 1119.
10. Genet, J.-P.; Juge, S.; Achi, S.; Mallart, S.; Montes, J. R.; Levif, G. Tetrahedron 1988, 44, 5263.
11. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
12. Carter, M. J.; Fleming, I.; Percival, A. J. Chem. Soc, Perkin Trans. 1 1981, 2415.
13. Though convenient, addition of sodium potassium tartrate solution to dissolve the aluminum salts followed by a standard extractive workup consistently afforded lower product yields. Addition of MgSO4 to the precipitated salts facilitated filtration.
14. Some aromatization to p-methylphenol occurred when 5 was treated with stronger acid (p-TsOH), although 1 was still obtained as the major product. No aromatization occurred when PPTS or oxalic acid was used.