Studies on electrocyclization in bicyclo[4.4.1]undeca-2,4-diene and bicyclo[4.2.1]nona-2,4-diene systems

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2553-2556

  Rigby, James H ^a   De Sainte Claire, Valérie ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; BICYCLO[4.2.1]NONANE DERIVATIVE; BICYCLO[4.4.1]UNDECANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029887621     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00328-0     Document Type: Article

References (11)

1. Rigby, J. H. Acc. Chem. Res. 1993, 26, 579.
2. For an example in another ring system, see: Lautens, M.; Kumanovic, S J. Am. Chem. Soc. 1995, 117, 1954 and references cited therein.
3. For related electrocyclizations, see: a) Mukai, T.; Akasaki, Y.; Hagiwara, T. J. Am. Chem. Soc. 1972, 94, 675.
4. b) Jefford, C. W.; Delay, F. Ibid. 1972, 94, 4794.
5. Hahn, R. C.; Johnson, R. P. Ibid. 1975, 97, 212.
6. Jefford, C. W.; Delay, F. Ibid. 1975, 97, 2272.
7. 13C NMR, IR) and analytical (HRMS and/or combustion analysis) data consistent with the assigned structure.
8. The structure of this compound was established by single crystal x-ray analysis of the corresponding diacetate derivative.
9. General procedure for electrocyclization of dienes: The diene was dissolved in a small amount of an appropriate solvent (hexanes, ether or dichloromethane) and introduced along with 320 mL of hexanes into a dry photochemical reaction vessel equipped with a quartz glass immersion well. Argon was bubbled vigorously through the solution for 15 min., and then the reaction mixture was irradiated (Canrad-Hanovia 450 W medium pressure mercury vapor lamp) for 15 min. The solvent was removed in vacua and the residue chromatographed with the appropriate eluent.
10. Zhai, D.; Zhai, W.; Williams, R. M. J. Am. Chem. Soc. 1988, 110, 2501.
11. Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495.