The crystal structure and characteristic chemical property of 1,2-bis(3-guaiazulenylmethylium)benzene bishexafluorophosphate

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 275-279

  Sasaki, Masato ^a   Nakamura, Masaru ^a   Hannita, Gen ^a   Takekuma, Hideko ^a   Minematsu, Toshie ^a   Yoshihara, Masakuni ^a   Takekuma, Shin Ichi ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

Azulenes; Carbonium ions; Reduction; X ray crystal structures

Indexed keywords

1,2 BIS(3 GUAIAZULENYLMETHYLIUM)BENZENE BISHEXAFLUOROPHOSPHATE; ACETONITRILE; ALCOHOL; BENZENE DERIVATIVE; ETHER; HEXAFLUOROPHOSPHORIC ACID; PHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CYCLOADDITION; MASS SPECTROMETRY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; REDUCTION; TEMPERATURE;

EID: 0037421072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02560-1     Document Type: Article

References (11)

1. Takekuma S., Takata S., Sasaki M., Takekuma H. Tetrahedron Lett. 42:2001;5921-5924.
2. Takekuma S., Sasaki M., Takekuma H., Yamamoto H. Chem. Lett. 1999;999-1000.
3. Takekuma, S.; Tanizawa, M.; Sasaki, M.; Matsumoto, T.; Takekuma, H. Tetrahedron Lett. 2002, 43, 2073-2078. Crystallographic data of compound 4 have been deposited at the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK and copies can be obtained on request, free of charge, by quoting the publication citation and the deposition number CCDC 184618.
4. Sasaki, M.; Nakamura, M.; Uriu, T.; Takekuma, H.; Minematsu, T.; Yoshihara, M.; Takekuma, S. Tetrahedron, submitted for publication. The deposition number CCDC of the crystallographic data for compound 5: 190065.
5. 2CH-7′,7′′) and 13.8 (Me-1′,1′′).
6. Compound 6 was prepared by the following procedure: To a solution of guaiazulene (1) (100 mg, 0.50 mmol) in methanol (1.5 mL) as added a solution of benzaldehyde (80 μL, 0.77 mmol) in methanol (0.5 mL) containing hexafluorophosphoric acid (60% aqueous solution, 0.2 mL). The mixture was stirred at 25°C for 1.5 h under aerobic conditions, giving a precipitation of a reddish-orange solid of 6, which was centrifuged at 2.5 krpm for 1 min. The crude product thus obtained was carefully washed with diethyl ether, and was recrystallized from acetonitrile-diethyl ether (1:4, vol/vol) (several times) to provide stable single crystals (208 mg, 0.48 mmol, 96% yield) suitable for X-ray crystallographic analysis.
7. 2=0.217. Goodness of Fit indicator=1.58.
8. 2=0.243. Goodness of Fit indicator=2.21.
9. Zeller K.-P. 4th ed. Methoden der Organishen Chemie. V/2c:1985;127 Georg Thieme Verlag, Stuttgart.
10. Recently the isolated yield of compound 7 has increased to 30% by careful chromatographic purification.
11. 2CH-7′,7′′) and 12.6 (Me-1′,1′′).