Unambiguous detection of 2,4,6-cycloheptatrien-1-ol by NMR spectroscopy and trapping with phenyltriazolinedione

Tetrahedron

Volumn 59, Issue 6, 2003, Pages 795-800

  Oda, Mitsunori ^a   Okawa, Kazuya ^a   Tsuri, Hitoshi ^a   Kuroda, Shigeyasu ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Alcohol; Carbocation; Cycloaddition; Phenyltriazolinedione; Tropylium ion

Indexed keywords

2,4,6 CYCLOHEPTATRIEN 1 OL; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ANION; CATION; CHLOROFORM; ETHER DERIVATIVE; HYDROXIDE; KETONE DERIVATIVE; PHENYLTRIAZOLINEDIONE; TRIAZOLINE DERIVATIVE; TROPONE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANALYTIC METHOD; AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; DISPROPORTIONATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037415493     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01617-4     Document Type: Article

References (16)

1. Franklin J.L. Olah G.H., Schleyer P.v R. Carbonium Ions. Vol. 1:1968;77-110 Interscience, New York. Chapter 2.
2. Sugihara Y., Kawanaka H., Murata I. Angew. Chem. 101:1989;1258-1259. Angew. Chem. Int. Ed. 1989, 28, 1258-1269.
3. For isomeric enol-type compounds, 1,3,5-cycloheptatrien-1-, -2-, and -3-ols, see: Lew C.S.Q., Capon B. J. Org. Chem. 62:1997;5344-5353.
4. Although an iron tricaronyl complex of 3 has been known, cleavage of iron from this complex for either detection or trapping was so far unsuccessfull despite our efforts. For the synthesis of this complex, see: Mayr H., Müller K.H., Ofinal A.R., Bühl M. J. Am. Chem. Soc. 121:1999;2418-2424.
5. Sugihara, Y.; Murata, I. Private communications.
6. Doering W.E., Knox L.H. J. Am. Chem. Soc. 76:1954;3203-3206. Doering W.E., Knox L.H. J. Am. Chem. Soc. 79:1957;352-356.
7. Doering W.E., Knox L.H. J. Am. Chem. Soc. 76:1954;3203-3206. Doering W.E., Knox L.H. J. Am. Chem. Soc. 79:1957;352-356.
8. Ikemi T., Nozoe T., Sugiyama H. Chem. Ind. (London). 1960;923 Borg A.P.T., Helden R.V., Bickel A.F., Renold W., Dreiding A.S. Helv. Chim. Acta. 1960;457-458 Machiguchi T. Synth. Commun. 12, 1982;1021-1025.
9. Ikemi T., Nozoe T., Sugiyama H. Chem. Ind. (London). 1960;923 Borg A.P.T., Helden R.V., Bickel A.F., Renold W., Dreiding A.S. Helv. Chim. Acta. 1960;457-458 Machiguchi T. Synth. Commun. 12, 1982;1021-1025.
10. Ikemi T., Nozoe T., Sugiyama H. Chem. Ind. (London). 1960;923 Borg A.P.T., Helden R.V., Bickel A.F., Renold W., Dreiding A.S. Helv. Chim. Acta. 1960;457-458 Machiguchi T. Synth. Commun. 12, 1982;1021-1025.
11. Franzus B., Shceinbaum M.L., Waters D.L., Bowlin H.B. J. Am. Chem. Soc. 98:1976;1241-1247.
12. Sasaki T., Kanematsu K., Hayakawa K. J. Chem. Soc. (C). 1971;2142-2147.
13. Cookson R.C., Gilani S.S.H., Stevens I.D.R. J. Chem. Soc. (C). 1967;1905-1909.
14. Adam, et al. prepared the exo-adduct of 7-methoxycycloheptatriene having a similar small coupling constant of 1.4 Hz Adam W., Balci M., Pietrzak B. J. Am. Chem. Soc. 101:1979;6285-6291.
15. Dauben H.J. Jr., Gadecki P.A., Harman M.K., Peason D.L. J. Am. Chem. Soc. 1957;1957-1958.
16. Cookson R.C., Gupte S.S., Stevens I.D.R., Watts C.T. Organic Synthesis. Coll. Vol. 6:1988;Wiley, New York.