M. Kosaka, S. Kuwahara, Masataka Watanabe, N. Harada, Gabriel E. Job, W. H. Pirkle
{"title":"比较(2-甲基苯基)-和(2,6-二甲基苯基)-苯甲醇的CD光谱会导致错误的绝对构型。","authors":"M. Kosaka, S. Kuwahara, Masataka Watanabe, N. Harada, Gabriel E. Job, W. H. Pirkle","doi":"10.1080/10242430212878","DOIUrl":null,"url":null,"abstract":"Enantiopure (2,6-dimethylphenyl)phenylmethanol (+)-(3) and analog (+)-(4) were prepared and their CD spectra were found opposite to that of (2-methylphenyl)phenylmethanol (R)-(-)-(2), the absolute configuration of which was previously established by X-ray crystallography. Therefore the S absolute configuration was once assigned to (+)-3 and (+)-4. After that we have succeeded in the X-ray analyses of chiral dichlorophthalate esters of (+)-3 and (+)4, which clearly indicated R absolute configuration. It is thus evident that comparison of the CD spectra of alcohols 2, 3, and 4 leads to erroneous absolute configurations.","PeriodicalId":11752,"journal":{"name":"Enantiomer","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2002-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"14","resultStr":"{\"title\":\"Comparison of CD spectra of (2-methylphenyl)- and (2,6-dimethylphenyl)-phenylmethanols leads to erroneous absolute configurations.\",\"authors\":\"M. Kosaka, S. Kuwahara, Masataka Watanabe, N. Harada, Gabriel E. Job, W. H. Pirkle\",\"doi\":\"10.1080/10242430212878\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Enantiopure (2,6-dimethylphenyl)phenylmethanol (+)-(3) and analog (+)-(4) were prepared and their CD spectra were found opposite to that of (2-methylphenyl)phenylmethanol (R)-(-)-(2), the absolute configuration of which was previously established by X-ray crystallography. Therefore the S absolute configuration was once assigned to (+)-3 and (+)-4. After that we have succeeded in the X-ray analyses of chiral dichlorophthalate esters of (+)-3 and (+)4, which clearly indicated R absolute configuration. It is thus evident that comparison of the CD spectra of alcohols 2, 3, and 4 leads to erroneous absolute configurations.\",\"PeriodicalId\":11752,\"journal\":{\"name\":\"Enantiomer\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2002-07-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"14\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Enantiomer\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1080/10242430212878\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Enantiomer","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1080/10242430212878","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
Comparison of CD spectra of (2-methylphenyl)- and (2,6-dimethylphenyl)-phenylmethanols leads to erroneous absolute configurations.
Enantiopure (2,6-dimethylphenyl)phenylmethanol (+)-(3) and analog (+)-(4) were prepared and their CD spectra were found opposite to that of (2-methylphenyl)phenylmethanol (R)-(-)-(2), the absolute configuration of which was previously established by X-ray crystallography. Therefore the S absolute configuration was once assigned to (+)-3 and (+)-4. After that we have succeeded in the X-ray analyses of chiral dichlorophthalate esters of (+)-3 and (+)4, which clearly indicated R absolute configuration. It is thus evident that comparison of the CD spectra of alcohols 2, 3, and 4 leads to erroneous absolute configurations.