Synthesis and characterization of both enantiomers of trans-1,2-di-(2-hydroxy-2-propyl)-cyclobutane

Tetrahedron Asymmetry

Volumn 7, Issue 10, 1996, Pages 2957-2961

  Curtius, Frank W ^a   Scharf, Hans Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030272838     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00386-2     Document Type: Article

References (18)

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3. 3. Goldworthy, L.J. Journal Chem. Soc. 1924, 2012.
4. 4. Kipping, F.B.; Wren, J.J. Journal Chem. Soc. 1957, 3246.
5. 5. Brunet, J.J.; Herbowsky, A.; Neibecker, D. Synthetic Communications 1996, 26, 483.
6. 6. Bourguignon, J.J.; Wermuth, G.C. J. Org Chem. 1981, 46, 4889.
7. 7. For another way of preparation see: Farina, Martin y Martin Anales de Quimica 1978, 74, 799.
8. 8. a) Feringa, B.L; Lange, B. de; Jong, J.C. de J. Org Chem. 1989, 54, 2471.
9. b) Martin, M.R.; Mateo, A.I. Tetrahedron: Asymmetry 1994, 5, 1385.
10. 9. For an introduction in organic photochemistry and preparative techniques see for example: J. Kopécky ; Organic Photochemistry. A visual approach 1992 VCH Publishers, Inc. and literatur cited therein.
11. 10. H. Haken, H. C. Wolf; Atom-und Quantenphysik 1983 , Springer-Verlag, Berlin.
12. 11. a) Hoffmann, N.; Scharf, H.-D.; Runsink, J. Tetrahedron Lett. 1989, 30, 2637.
13. b) Hoffmann, N, Buschmann, H., Raabe, G., Scharf, H.-D. Scharf, H.-D. Tetrahedron 1994, 50, 11167.
14. c) Alibés, R.; Bourdelande, J. L.; Font, J.; Gregori, A; Parella,T. Tetrahedron 1996, 52, 1267
15. 12. Imamoto, T.; Kusumoto, T.; Tawarayama, Y; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokojama, M.J. Org Chem. 1984, 49, 3904
16. 13. Hoffmann, N. Dissertation 1992 RWTH Aachen.
17. 3): δ = 102.17, 83.64, 73.39, 57.63, 33.26, 29.14, 23.45, 16.53 ppm. The hydroxyd-proton appears in the region of 4 ppm.
18. 1H-NMR-spectrum only the acetalic proton [5.86 (d, J = 1Hz, 1H) ppm] and the C-1-proton of the cyclohexan ring [3.65 (d / t, 4.5 / 10.5Hz, 1H) ppm] were clearly different to those of 4a.