Regio- and stereocontrolled synthesis of (2R*,3R*,4R*)-3, 4-dichloro-1,2,3,4,5,8-hexahydronaphthalen-2-yl acetate via tandem S N2′ reactions

Helvetica Chimica Acta

Volumn 89, Issue 6, 2006, Pages 1246-1253

  Horasan Kishali, Nurhan ^a   Sahin, Ertan ^a   Kara, Yunus ^a  

^a ATATÜRK UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROPEROXY ENDOPEROXIDE; MECHANISTIC RATIONALIZATION; PHOTOOXYGENATION;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SINGLE CRYSTALS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

ORGANIC COMPOUNDS;

1,2,5,8, TETRAHYDRONAPHTHALENE 2,4,A,8A TRIOL; 3,4, DICHLORO 1,2,3,4,5,8 HEXAHYDRONAPHTHALENE 2 YL ACETATE; 9,10 DIOXATRICYCLO[6.2.2.0 1.6]DODECA 3,11 DIEN 6 YL HYDROPEROXIDE; ACETIC ACID; ACETIC ACID DERIVATIVE; CHLORIDE; CYCLOHEXANE DERIVATIVE; ISOTETRALIN; THIOUREA; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOOXIDATION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 33745756126     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690122     Document Type: Article

References (18)

1. a) A. A. Frimer, 'Singlet Oxygen: Reaction Modes and Products', CRC Press: Boca Raton, FL, 1985, Vol. 2/Part 1, Vol. 3/Part 2;
2. b) 'The Chemistry of Functional Groups: Peroxides'; Ed. S. Patai, J. Wiley & Sons, New York, 1983;
3. H. H. Wasserman, 'Singlet Oxygen', Ed. W. M. Murray, Academic Press, New York, 1979;
4. M. Balci, Chem. Rev. 1981, 81, 91;
5. e) E. L. Clennan, A. Pace, Tetrahedron 2005, 61, 6665.
6. C. S. Foote, Science 1970, 162, 963;
7. C. S. Foote, W. A. Pryor, in 'Free Radicals in Biology', Academic Press, New York, 1976, Vol. 2, p. 85;
8. T. Wilson, J. W. Hastings, Photophysiology 1970, 5, 49.
9. H. Seçen, E. Salamci, Y. Sütbeyaz, M. Balci, Synlett 1993, 609;
10. E. Salamci, H. Sȩen, Y. Sütbeyaz, M. Balci, J. Org. Chem. 1997, 62, 2453;
11. Y. Kara, M. Balci, Tetrahedron 2003, 59, 2063;
12. L. Kelebekli, Y. Kara, M. Balci, Carbohydr. Res. 2005, 340, 1940;
13. M. S. Gültekin, M. Celik, M. Balci, Curr. Org. Chem. 2004, 8, 1159.
14. N. H. Kishali, E. Sahin, Y. Kara, Org. Lett., 2006, 60, 1791.
15. A. Baran, C. Kazaz, H. Seçen, Tetrahedron 2004, 60, 861.
16. D. Cremer, J. A. Pople, J. Am. Chem. Soc. 1975, 97, 1354.
17. Rigaku/MSC, Inc., 9009 New Trails Drive, The Woodlands, TX 77381, U.S.A.
18. G. H. Sheldrick, SHELXS-97 and SHELXL-97, University of Göttingen, Germany, 1997.