Different Z/E-selectivity depending upon the length of the acyl side chain in the formation of 2,2′-diacyl-9,9′-bifluorenylidene

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 2, 2006, Pages 333-335

  Oota, Atsushi ^a   Imai, Toshinobu ^a   Yamazaki, Ayumi ^a   Oba, Toru ^a   Karikomi, Michinori ^a   Minabe, Masahiro ^a  

^a UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROBROMINATION; STEREO-SELECTIVITY;

DERIVATIVES; ISOMERIZATION; ISOMERS; STEREOCHEMISTRY;

ORGANIC COMPOUNDS;

2 ACYL 9 BROMOFLUORENE; 2,2' DIACYL 9,9' BIFLUORENYLIDENE; 9 BROMO 9,9' BIFLUORENYL; FLUORENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DIASTEREOISOMER; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 33750559357     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.333     Document Type: Article

References (12)

1. H. E. Bronstein, N. Choi, L. T. Scott, J. Am. Chem. Soc. 2002, 124, 8870.
2. E. Bergmann, J. Hervey, Ber. Dtsch. Chem. Ges. 1929, 62, 893.
3. M. Minabe, K. Suzuki, Bull. Chem. Soc. Jpn. 1975, 48, 586.
4. D. Bethell, J. Chem. Soc. 1963, 666.
5. D. Bethell, A. F. Cockerill, J. Chem. Soc. B 1966, 917.
6. D. Bethell, A. F. Cockerill, D. B. Frankham, J. Chem. Soc. B 1967, 1287.
7. M. Minabe, T. Oba, M. Tanaka, K. Kanno, M. Tsubota, Chem. Lett. 2000, 498.
8. R. Stösser, J.-U. Thurner, G. Tomaschewski, U. Ewert, P. Heblik, W. Schneider, T. Hanke, Z. Naturforsch. A: Phys. Sci. 1982, 37, 1241.
9. J. Schmidt, H. Wagner, Ber. Dtsch. Chem. Ges. 1910, 43, 1797.
10. Ketone 6a should be formed via air-oxidation of 2, 3, and 1 in the presence of base. A large excess of solvent resulted in an increase of the oxidized compound 6 (see Run 2 in Table 1). A part of 6 should be formed via 9-fluorenol that was generated from 2 in the presence of potassium carbonate as a contaminant of potassium hydroxide.
11. Separation and characterization of the pure threo- and erythro-3, and the related compounds are now in progress. 12 Colorless or light yellowish 2, 3, 5, and 6 did not give absorption bands at this wavelength region.
12. -6 M, respectively.