Oxidative scission of ethyl 2,2-dimethoxycyclopropanecarboxylates with lead tetraacetate. Synthesis of the unusual anhydride bis-acetals

Tetrahedron Letters

Volumn 40, Issue 48, 1999, Pages 8469-8470

  Graziano, M Liliana ^a   Piccialli, Vincenzo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Anhydride bis acetals; Fumarates; Lead tetraacetate; Vicinally substituted donor acceptor cyclopropanes

Indexed keywords

ACETAL DERIVATIVE; ACETIC ANHYDRIDE; CYCLOPROPANE DERIVATIVE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; FUMARIC ACID DERIVATIVE; LEAD ACETATE;

ARTICLE; CHEMICAL STRUCTURE; DECARBOXYLATION; LYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0033607427     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01776-1     Document Type: Article

References (10)

1. For a review, see Reißig, H.-U. Top. Curr. Chem. 1988, 144,73-135.
2. For previous papers on this topic, see Graziano, M. L.; Iesce, M. R.; Cermola, F. J. Chem. Res 1996, (S) 82, (M) 622 and references therein.
3. Graziano, M. L.; Lasalvia, M.; Piccialli, V.; Sica, D. Tetrahedron Lett. 1996, 4, 527-530.
4. For general accounts on LTA reactions, see: (a) Criegee, R. In Oxidation in Organic Chemistry, Wiberg, K. B., Ed., Academic Press: New York, 1965; Part A.
5. (b) Sheldon, R. A.; Kochi, J. K. Org. Reac. 1972, 19, 279-421.
6. (c) Mihailovic, M. L.; Cekovic, Z.; Lorenc, L. In Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J.; De Jonge, C. R. H.I., Eds.; Plenum Press: New York, 1986, pp. 741-816.
7. Bornstein, D.; Weisz, A.; Mandelbaum, A. Org. Mass. Spectrom. 1986, 21, 225-228.
8. Elemental analysis has been performed at the Analytische Laboratorien GMBH, Germany.
9. (a) Doebner, O. Justus Liebigs Annalen der Chimie 1890, 256, 56-60.
10. (b) Castellano, J. A. J. Org. Chem. 1972, 37, 3151-3160.