Stereoselectivity in the Fe(II)/Cu(II)-mediated homolytic decomposition of the cis- and trans-isomers of pinane hydroperoxide

Chemistry Letters

Volumn , Issue 8, 2002, Pages 830-831

  Lempers, H E B ^a   Sheldon, R A ^a   Swift, K A D ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,2 DIMETHYL 3 VINYLCYCLOBUT 1 YL)ETHANONE; 1,4 DIMETHYL 3 OXATRICYCLO[5.2.0.0 4,9]NONANE; ALKANE DERIVATIVE; COPPER; COPPER SULFATE; FERROUS ION; HYDROGEN; HYDROPEROXIDE DERIVATIVE; PINANE HYDROPEROXIDE; RADICAL; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIS ISOMER; DECOMPOSITION; DIMERIZATION; OXIDATION; STEREOCHEMISTRY; TRANS ISOMER;

EID: 0037025517     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.830     Document Type: Article

References (10)

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3. H. E. B. Lempers, Ph. D. Thesis, Delft University, Delft, The Netherlands, 1998.
4. H. E. de la Mare, J. K. Kochi, and F. F. Rust, J. Am. Chem. Soc., 85, 1473 (1963).
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6. J. K. Kochi, J. Am. Chem. Soc., 85, 9163 (1958).
7. W. F. Erman, "Chemistry of the Monoterpenes, Part A," Marcel Dekker Inc., New York (1997), p 1363.
8. 3) δ 88.2, 48.9, 40.9, 38.2, 27.7, 27.5, 27.1, 25.3, 24.1, 23.0. GC/MS m/z (%) after reduction with tributylphosphine 154 (13), 139 (28), 136 (18), 109 (78), 84 (100).
9. 3) δ 207.8, 137.4, 115.8, 54.0, 45.5, 44.9, 30.1, 30.1, 21.9, 18.0. GC/MS m/z (%) 152 (10), 137 (15), 118 (34) 70 (100).
10. 3) δ 87.7, 72.6, 52.3, 51.9, 41.3, 32.1, 25.6, 22.8, 22.9, 19.7. GC/MS m/z (%) 152 (7) 137 (15), 122 (34), 84 (100).