Oxidative rearrangement of bicyclo[n.1.0]alkan-1-ols in the presence of oxygen

Tetrahedron Letters

Volumn 40, Issue 21, 1999, Pages 4045-4046

  Morisson, Véronique ^a   Barnier, Jean Pierre ^a   Blanco, Luis ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[N.1.0]ALKAN 1 OL; CYCLOALKANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COLUMN CHROMATOGRAPHY; DRUG ISOLATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; PEROXIDATION; REACTION ANALYSIS;

EID: 0033591153     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00667-X     Document Type: Article

References (8)

1. 1. Morisson, V.; Baraier, J.-P.; Blanco, L. Tetrahedron 1998, 54, 7749-7764.
2. 2. Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. J. Chem. Soc., Chem. Commun. 1998, 1691-1692.
3. 3. Rf values on silica-gel plates (pentane/ether: 1/1) 1b: 0.52; 2: 0.38; 3b: 0.33; 4b: 0.12.
4. 4. The formation of a 3-hydroperoxyalkanoate by treatment of cyclopropanone hemiketal with atmospheric oxygen was reported: Gibson, D.H.; DePuy, C.H. Tetrahedron Lett. 1969, 2203-2206. A cyclic peroxyhemiketal was isolated after photooxygenation of a cyclopropanol derivative in conditions where singlet oxygen could be generated: Scheller. M.-E.; Mathias, P.; Petter, W. Helv. Chim. Acta 1984, 67, 1748-1754.
5. 4. The formation of a 3-hydroperoxyalkanoate by treatment of cyclopropanone hemiketal with atmospheric oxygen was reported: Gibson, D.H.; DePuy, C.H. Tetrahedron Lett. 1969, 2203-2206. A cyclic peroxyhemiketal was isolated after photooxygenation of a cyclopropanol derivative in conditions where singlet oxygen could be generated: Scheller. M.-E.; Mathias, P.; Petter, W. Helv. Chim. Acta 1984, 67, 1748-1754.
6. 5. New compounds were characterized on the basis of IR and NMR spectral data and elemental analysis.
7. 6. In these reaction mixtures the corresponding 3-hydroxycycloalkanone was always obtained (up to 34% in the case of 3a), along with some cycloalk-2-enone and unidentified by-products.
8. 7 The presence of the enone 2 was also noticed in these conditions.