Wei Rong-bao
2010
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Journal
Journal of tianjin University of Technology
Abstract
The compounds of 3,15-bis{8-(1,4-dioxaspiro[4.5]decyl)-7,11,18,21-tetraoxa-trispiro[5.2.2.5.2.2] heni-cosane(1) and 3,15-poly{7,11,18,21-tetraoxa-trispiro[5.2.2.5.2.2] henicosane(2) were synthesized by reaction of di(cyclohexane)-4,4’-dione mono ketal with 2,2-bis(hydroxymethyl)-1,3-propanediol at the presence of I2or InBr3.The1HNMR characterization of the compounds were discussed.In the 1H-NMR spectra,the signals of eight hydrogen atoms of methylene groups(2H8,2H10,2H19,2H20) in chiral axis-containing compounds 1 and 2 were not split and singlet peak,butthe corresponding signal of the hydrogen atoms was four groups of doublets in compound of 3,9-diphenyl-2,4,8,10-tetraoxa-spiro[5.5]undecane.The signals of hydrogen atoms of methylene groups(H1,H5,H13,H17) were not split into multiplepeak,owing to the influence by chiral axis and adjacent CH2.It was indicated that the effect of chiral axes to chirality is at out-board.The result has a wider significance to design chiral catalyst and chiral stationary phase for chiral synthesis.