(Hydroxyphenyl)carbenes

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4460-4461

  Golden, Adam H ^a   Jones Jr , Maitland ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012639560     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952003d     Document Type: Article

References (14)

1. Portions of this work are taken from the A.B. Thesis of Adam H. Golden, Princeton University, 1986. We thank the National Science Foundation for support through grants CHE 83-18345 and CHE9322579.
2. Very similar results have been obtained in the laboratories of Harold Shechter at The Ohio State University. We thank professor Shechter for stimulating conversations, for sharing his data, and for agreeing to simultaneous publication.
3. Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and references therein.
4. For two examples of the phenylcarbene rearrangement used as a "divalency transport system", see: Chambers, G. R.; Jones, M., Jr. Tetrahedron Lett. 1978, 5193. Boxberger, M.; Volbracht, L.; Jones, M., Jr. Tetrahedron Lett. 1980, 3669.
5. For two examples of the phenylcarbene rearrangement used as a "divalency transport system", see: Chambers, G. R.; Jones, M., Jr. Tetrahedron Lett. 1978, 5193. Boxberger, M.; Volbracht, L.; Jones, M., Jr. Tetrahedron Lett. 1980, 3669.
6. Gleiter, R.; Rettig, W.; Wentrup, C. Helv. Chim. Acta 1974, 57, 2111. Decomposition of the o-tetrazole leads only to the corresponding nitrile. Apparently the proximate OH catalyzed the reverse cycloaddition. At any rate, no sign of carbene chemistry appears.
7. Wentrup, C. In Methoden der Organische Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme Verlag: Stuttgart, 1989; Vol. E19b, pp 824-976. Platz, M. S.; Maloney, V. M. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; Chapter 8.
8. Wentrup, C. In Methoden der Organische Chemie (Houben-Weyl); Regitz, M., Ed.; G. Thieme Verlag: Stuttgart, 1989; Vol. E19b, pp 824-976. Platz, M. S.; Maloney, V. M. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum Press: New York, 1990; Chapter 8.
9. Tomioka, H.; Taketsuji, K. J. Org. Chem. 1993, 58, 4196.
10. Wentrup, C.; Becker, J. J. Am. Chem. Soc. 1984, 106, 3705.
11. Dunkin, I. R.; El Ayeb, A.; Lynch, M. A. J. Chem. Soc., Chem. Commun. 1994, 1695.
12. Paul, G. C.; Gajewski, J. J. J. Org. Chem. 1993, 58, 5060.
13. Sekiguchi, A.; Ando, W. Bull, Chem. Soc. Jpn. 1977, 50, 3067.
14. Crow, W. D.; McNab, H. Aust. J. Chem. 1979, 32, 99.