The preparation of substituted phenanthrenes from aryl pinacols in superacid

Synthesis

Volumn , Issue 3, 1996, Pages 321-323

  Olah, G A ^a   Klumpp, D A ^a   Neyer, G ^a   Wang, Q ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

aryl pinacols; phenanthrenes; superacid; triflic acid

Indexed keywords

PHENANTHRENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030000570     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4225     Document Type: Article

References (10)

1. Rickborn, B. In Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: Oxford, 1991, Vol. 3, 721.
2. (a) Schmidlin, J.; Escher, R. Ber. Dtsch. Chem. Ges. 1910, 43, 1153.
3. (b) Schoepfle, C.S.; Ryan, J.D. J. Am. Chem. Soc. 1932, 54, 3687.
4. (a) Schonberg, A.; Mustafa, A. Chem. Rev. 1947, 40, 181.
5. (b) Gilbert, A.; Baggot, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991.
6. (a) Olah, G.A. Angew. Chem. 1993, 105, 805; Angew. Chem., Int. Ed. Engl. 1993, 32, 767.
7. (a) Olah, G.A. Angew. Chem. 1993, 105, 805; Angew. Chem., Int. Ed. Engl. 1993, 32, 767.
8. (b) Saito, S.; Sato, Y.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1994, 116, 2312.
9. Aryl pinacols were synthesized by photolysis of substituted benzophenones dissolved (0.1 M) in degassed isopropanol. Photolysis was done with a 450 W Hanovia medium pressure mercury lamp. The pinacols usually precipitated from solution and were isolated by filtration.
10. Bacon, R.G.R.; Lindsay, W.S. J. Chem. Soc. 1958, 1382.