On the di-1-naphthylcarbene-dibenzofluorene rearrangement and the ethylenization of diarylcarbinols

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8417-8423

  Régimbald Krnel, Michèle ^a   Wentrup, Curt ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLIZATION; DEHYDRATION; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032515002     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981397g     Document Type: Article

References (40)

1. Staudinger, H.; Endle, R. Ber. Dtsch. Chem. Ges. 1913, 46, 1437-1442. The reaction was also formulated in that way by Harrison and Lossing (Harrison, H. D.; Lossing, P. F. J. Am. Chem. Soc. 1960, 82, 1052) (using bromodiphenylmethane as a thermal precursor of diphenylcarbene and fluorene) and by Rice and Michaelsen (Rice, F. O.; Michaelsen, J. D. J. Phys. Chem. 1962, 66, 1535) (using diphenyldiazomethane as a thermal precursor).
2. Staudinger, H.; Endle, R. Ber. Dtsch. Chem. Ges. 1913, 46, 1437-1442. The reaction was also formulated in that way by Harrison and Lossing (Harrison, H. D.; Lossing, P. F. J. Am. Chem. Soc. 1960, 82, 1052) (using bromodiphenylmethane as a thermal precursor of diphenylcarbene and fluorene) and by Rice and Michaelsen (Rice, F. O.; Michaelsen, J. D. J. Phys. Chem. 1962, 66, 1535) (using diphenyldiazomethane as a thermal precursor).
3. Staudinger, H.; Endle, R. Ber. Dtsch. Chem. Ges. 1913, 46, 1437-1442. The reaction was also formulated in that way by Harrison and Lossing (Harrison, H. D.; Lossing, P. F. J. Am. Chem. Soc. 1960, 82, 1052) (using bromodiphenylmethane as a thermal precursor of diphenylcarbene and fluorene) and by Rice and Michaelsen (Rice, F. O.; Michaelsen, J. D. J. Phys. Chem. 1962, 66, 1535) (using diphenyldiazomethane as a thermal precursor).
4. (a) Wentrup, C.; Wilczek, K. Helv. Chim. Acta 1970, 53, 1459-1463.
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7. For further reviews of carbene-carbene rearrangements, see also: Wentrup, C. Reactive Molecules; Wiley: New York, 1984. Jones, W. M. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic: New York, 1980; Vol. 1, pp 95-161. Wentrup, C. In Reactive Intermediates, Abramovitch, R. A., Ed.; Plenum: New York, 1980; Vol. 1, pp 263-319.
8. For further reviews of carbene-carbene rearrangements, see also: Wentrup, C. Reactive Molecules; Wiley: New York, 1984. Jones, W. M. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic: New York, 1980; Vol. 1, pp 95-161. Wentrup, C. In Reactive Intermediates, Abramovitch, R. A., Ed.; Plenum: New York, 1980; Vol. 1, pp 263-319.
9. For further reviews of carbene-carbene rearrangements, see also: Wentrup, C. Reactive Molecules; Wiley: New York, 1984. Jones, W. M. In Rearrangements in Ground and Excited States; de Mayo, P. Ed.; Academic: New York, 1980; Vol. 1, pp 95-161. Wentrup, C. In Reactive Intermediates, Abramovitch, R. A., Ed.; Plenum: New York, 1980; Vol. 1, pp 263-319.
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13. Wong, M. W.; Wentrup, C. To be published.
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28. At best, only traces of tetraarylethylenes are formed. The analogous reaction of diphenylcarbinol with hot phosphoric acid gave a trace (≤0.1%) of tetraphenylethylene, identifiable only by GC-MS.
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