Synthesis of 2,3-substituted cycloalkanones by ceric ammonium nitrate-promoted oxidative tandem additions of 1-ethoxy-1-[(trimethylsilyl)oxy]cyclopropane to α,β-unsaturated cycloalkenones

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6434-6437

  Paolobelli, Anna Belli ^a   Ruzziconi, Renzo ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011442578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960446r     Document Type: Article

References (16)

1. (a) Schaafsma, S. E.; Molenaar, E. J. F.; Steinberg, H.; de Boer, Th. J. Red. Trav. Chim. Pays-Bas 1968, 87, 1301.
2. (b) Schaafsma, S. E.; Jorritsma, R.; Steinberg, H.; de Boer, Th. J. Tetrahedron Lett. 1973, 827.
3. (a) Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193.
4. (b) Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Soc. Chim. Jpn 1993, 66, 819.
5. Belli Paolobelli, A.; Gioacchini, F.; Ruzziconi, R. Tetrahedron Lett. 1993, 34, 6333.
6. -1 for oxidation of the 1-hydroxyethyl radical to acetaldehyde by a variety of metals have been reported: Asmus, K.-D.; Bonifacic, M. In Landolt-Bornstein New Series, Group 2; Fischer, H., Ed.; Springer Verlag: Berlin, 1984; Vol. 13b, pp 311-313.
7. 2: Baciocchi, E.; Belli Paolobelli, A.; Ruzziconi, R. Tetrahedron 1992, 48, 4617.
8. • of ∼23 at 25°C for the hydrogen abstraction from ethanol can be estimated.
9. Thomas, J. K. J. Phys.Chem. 1967, 71, 1919
10. Indeed, acetonitrile proved to be a better solvent than methanol. In the latter solvent, substantial amounts of unidentified byproducts are also formed.
11. -1, respectively [Citterio, A.; Arnoldi, A.; Minisci, F. J. Org. Chem. 1979, 44, 2674
12. 8
13. Powdered calcium carbonate was also added in order to avoid the extensive solvolysis of 1 as well as the acetalization of vinyl ethyl ether catalyzed by the nitric acid produced by CAN in each oxidative process.
14. For example, a procedure could be envisaged, albeit a rather wearysome one, based on the copper(I)-catalyzed reaction of a zinc homoenolate (see: Nakamura, E.; Aoki, S.; Sekiya, K.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1987, 109, 8056) with the α,β-unsaturated cycloalkenone, followed by the addition of 2-(bromomethyl)-1,3-dioxolane or allyl bromide as electrophiles.
15. Baciocchi, E.; Casu, A.; Ruzziconi, R. Synlett 1990, 679.
16. The products turned brown in the long run at room temperature and upon exposure to the air.