Generation, characterization and some reactions of 1,1-ethylene-1H-azulenium ion

Chemistry Letters

Volumn , Issue 10, 1997, Pages 1011-1012

  Oda, Mitsunori ^a   Kajioka, Takanori ^a   Okujima, Tetsuo ^b   Itoh, Shunji ^b   Morita, Noboru ^b   Miyatake, Ryuta ^a   Kuroda, Shigeyasu ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 21944454913     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1011     Document Type: Article

References (20)

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13. 1H NMR spectrum of 7 showed an AB quartet at 4.58 ppm with a coupling constant of 15.0 Hz under irradiation at δ 2.88 ppm and also an AB quartet at 2.88 ppm with a coupling constant of 14.4 Hz under that at 4.58 ppm. Both the difference of geminal coupling constants between these methylene protons and the vicinal coupling manner of them indicate that the cyclobutane ring of 7 is fairly disordered in its strained ring system.
14. For synthesis and chemical reactions of spiro[2,4]hepta-4,6-dienes, see; L. G. Menchikov and O. M. Nefedov, Russ. Chem. Rev., 63, 449 (1994)
15. For other example of structural elucidation for an unstable cationic species by the pulsed field gradient method, see T. Nozoe, K. Shindo, H. Wakabayashi, T. Kurihara, and J. Uzawa, Chem. Lett., 1995, 687.
16. After completion of the rearrangement, the color of the solution turned dark brown.
17. Addition of ether to the solution of 1b and 5 at -20°C gave greenish solids. However, several efforts for purification of them by filtration and recrystalization at low temperature under inert atmosphere have met with little success so far.
18. A. G. Anderson, Jr., R. G. Anderson, and T. S. Fujita, J. Org. Chem., 27, 4535 (1962).
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