Catalytic deallylation of allyl- and diallylmalonates

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10222-10223

  Nečas, David ^a   Turský, Matyáš ^a   Kotora, Martin ^a,b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ALLYLMALONIC ACID DERIVATIVE; ALUMINUM DERIVATIVE; BROMIDE; CHLORIDE; DIALLYLMALONIC ACID DERIVATIVE; MALONIC ACID DERIVATIVE; METAL COMPLEX; NICKEL COMPLEX; RUTHENIUM COMPLEX; TRANSITION ELEMENT; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; DEALLYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 4143056958     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047320t     Document Type: Article

References (23)

1. (a) Bishop, K. C., III. Chem. Rev. 1976, 76, 461-486.
2. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245-269.
3. (c) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241-2290.
4. (d) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97-129.
5. (a) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471-6473.
6. (b) Bunel, E.; Burger, B. J.; Bercaw, J. E. J. Am. Chem. Soc. 1988, 110, 976-978.
7. (c) Kesti, M. R.; Waymouth, R. M. J. Am. Chem. Soc. 1992, 114, 3565-3567.
8. (d) Yang, X.; Li, J.; Marks, T. J. J. Am. Chem. Soc. 1993, 115, 3392-3393.
9. (e) Hajela, S.; Bercaw, J. E. Organometallics 1994, 13, 1147-1154.
10. (f) Rossier, C.; Niccolai, G. P.; Basset, J.-M. J. Am. Chem. Soc. 1997, 119, 12408-12409.
11. For Ni-catalyzed rearrangement of 1,4-dienes, see: (a) Miller, R. G. J. Am. Chem. Soc. 1967, 89, 2785-2787.
12. (b) Miller, R. G.; Pinke, P. A.; Baker, D. J. J. Am. Chem. Soc. 1970, 92, 4490-4492.
13. (c) Gosser, L. W.; Parshall, G. W. Tetrahedron Lett. 1971, 2555-2558.
14. (d) Miller, R. G.; Golden, H. J.; Baker, D. J.; Stauffer, R. D. J. Am. Chem. Soc. 1971, 93, 6308-6304.
15. (e) Miller, R. G.; Pinke, P. A.; Stauffer, R. D.; Golden, H. J.; Baker, D. J. J. Am. Chem. Soc. 1974, 96, 4211-4220.
16. For Pd-catalyzed Cope rearrangement of 1,5-dienes, see: (f) Overman, L. E.; Renaldo, A. F. J. Am. Chem. Soc. 1990, 112, 3945-3949.
17. (g) Hill R. K. in Comprehensive Organic synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5; pp 799-802.
18. Kondo, T.; Kodoi, K.; Nishihara, E.; Okada, T.; Morisaki, Y.; Watanabe, Y.; Mitsudo, T. J. Am. Chem. Soc. 1998, 120, 5587-5588.
19. Nečas, D.; Kotora, M.; Císařová, I. Eur. J. Org. Chem. 2004, 1280-1285.
20. Yamazaki, T.; Kasatkin, A.; Kawanaka, Y.; Sato, F. J. Org. Chem. 1996, 61, 2266-2267.
21. Oppolzer, W.; Schröder, F. Tetrahedron Lett. 1994, 35, 7939-7942.
22. 1H NMR spectroscopy.
23. (E)-1-Propenylbenzene was found as the side product of the deallylation of 1g and 1h.). An independent experiment showed that allylbenzene 6, the side product of the deallylation of lg, is quickly isomerized into (E)-1-propenylbenzene under the reaction conditions.