The first enantiomerically pure, C2-symmetric spiroselenurane: 3,3,3′,3′-tetramethyl-1,1′-spirobi[3H,2,1]-benzoxaselenole

Tetrahedron Asymmetry

Volumn 13, Issue 19, 2002, Pages 2079-2082

  Drabowicz, Józef ^a   Luczak, Jerzy ^a   Mikolajczyk, Marian ^a   Yamamoto, Yohsuke ^b   Matsukawa, Shiro ^b   Akiba, Kin ya ^c  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b HIROSHIMA UNIVERSITY   (Japan)

^c WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3,3,3',3' TETRAMETHYL 1,1' SPIROBI[3H,2,1]BENZOXASELENOLE; SPIRO COMPOUND; SPIROSELENURANE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CHROMATOGRAPHY; CIRCULAR DICHROISM; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; POLARIMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

EID: 0037020428     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00550-5     Document Type: Article

References (18)

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12. Drabowicz, J.; Mikolajczyk, M.; unpublished results.
13. 3 as an internal reference.
14. 3 solution on a JOEL 400 MHz AL400S spectrometer equipped with a pulse field gradient triple resonance probe.
15. max=56.00) were used for the solution of the structure. R=0.0445, wR=0.0737. No. of parameters refined 379. Goodness of fit (obsd)=1.078. Selected bond lengths [Δ] bond angles [°], torsion angles [°]: Se1-O1 1.933(2), Se1-O2 1.958(2), Se1-C1 1.940(2), Se1-C10 1.949(2); O1-Se1-O2 172.55(8), O1-Se1-C1 83.75(10), O1-Se1-C10 92.30(10), Se1-O1-C7-C6 74(3), S1-O1-C7-C8 128.7(2), Se1-C1-C2-C3 178.5(2), Se1-C1-C6-C5 179.5(2).
16. The chromatographic resolutions were carried out on a 4.6 mm ID×250 mm analytical column. Chiral pack AS, available from Daicel Chemical Industries Ltd., Japan. using a JASCO PH-980 HPLC pomp, a JASCO UV-vis-970 detector and a Shimadzu C-RA chromatopic recorder. The mobile phases used were hexane +1.0 to 20% of 2-propanol. UV detection at 225 nm. There was no resolution when hexane containing 2.5-10% of ethanol as the mobile phases were used. Very poor resolutions were observed on a 4.6 mm ID×250 mm analytical column, Chiralpack OP.
17. Polarimetric measurements were carried out on a Perkin-Elmer 241 photopolarimeter.
18. The CD spectra were recorded in hexane solutions on a CD 6 dichrograph (Jobin-Yvon) using cells with 5 mm path length.