The first reported halogenation of a tert-butyl group with HCl or HBr in CHCl3. Unexpected differences in the reactions of HCl, HBr, HI, and HF with sp-9-(o-tert-butylphenyl)-9-fluorenol

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9444-9449

  Meyers, Cal Y ^a   Hou, Yuqing ^a   Lutfi, Hisham G ^a,b   Saft, Howard L ^a  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORM; HYDROBROMIC ACID; HYDROCHLORIC ACID; HYDROFLUORIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HALOGENATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION POTENTIAL;

EID: 0033601218     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9910280     Document Type: Article

References (22)

1. A major part of this work was carried out by Hou, Y. Ph.D. Dissertation, Southern Illinois University, Carbondale, IL, 1997.
2. (a) Meyers, C. Y.; Chan-Yu-King, R.; Wahner, A. P.; Manohar, S. K.; Carr, S. E.; Robinson, P. D. Acta Crystallogr. 1991, C47, 1236-1239.
3. (b) Meyers, C. Y.; Tunnell, J. L.; Robinson, P. D.; Hua, D. H.; Saha, S. Acta Crystallogr. 1992, C48, 1815-18.
4. (c) Robinson, P. D.; Lutfi, H. G.; Lim, L. W.; Meyers, C. Y. Acta Crystallogr. 1994, C50, 1728-1732.
5. (d) Meyers, C. Y.; Hou, Y.; Scott, D.; Robinson, P. D. Acta Crystallogr. 1997, C53, 1149-1151.
6. (e) Hou, Y.; Meyers, C. Y.; Robinson, P. D. Acta Crystallogr. 1998, C54, 1013-1016.
7. Robinson, P. D.; Hou, Y.; Meyers, C. Y. Acta Crystallogr. 1998, C54, 1173-1175.
8. Meyers, C. Y.; Hou, Y.; Lutfi, H. G.; Robinson, P. D. National Meeting of the American Chemical Society, Chicago, Aug 20-24, 1995; Abstract No. ORGN 297.
9. Meyers, C. Y.; Hou, Y.; Lutfi, H. G.; Robinson, P. D.; Dunn, H. E.; Seyler, J. W. National Meeting of the American Chemical Society, San Francisco, Apr 13-17, 1997, Abstracts ORGN 351.
10. Meyers, C. Y.; Hou, Y.; Robinson, P. D. Acta Crystallogr. 1999, C55, 626-628.
11. (a) Robinson, P. D.; Hou, Y.; Meyers, C. Y. Acta Crystallogr. 1998, C54, CIF Access paper, DVN IUC9800051.
12. (b) Hou, Y.; Meyers, C. Y. Can. J. Chem, 1999, 77, 960-966.
13. Robinson, P. D.; Hou, Y.; Lutfi, H. G.; Meyers, C. Y. Acta Crystallogr. 1998, C54, 73-77.
14. The designations sp (synperiplanar) and ap (antiperiplanar) for these fluorene rotamers are in accord with Rule E-6.6, IUPAC Tentative Rules, Section E, Fundamental Stereochemistry (J. Org. Chem. 1970, 35, 2861).
15. 1H NMR spectroscopy. The most striking differences emanate from the o-tert-butyl protons. In the ap rotomers these protons are shielded by the fluorene π electrons and resonate upfield in the 0.7 ppm region, while in the sp rotomers they are correspondingly deshielded and resonate downfield in the 1.8 ppm region. Differences are also observed in the resonances of the ortho-H of ap vs sp rotamers and of the H-9 of these rotamers of 9-(o-tert-butylphenyl)fluorene itself. See refs 1, 2d,e, 3, 6-8, and 11.
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