Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all atte...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2010-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.6.62 |
| _version_ | 1818919695724576768 |
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| author | Bruno Linclau Leo Leung Jean Nonnenmacher Graham Tizzard |
| author_facet | Bruno Linclau Leo Leung Jean Nonnenmacher Graham Tizzard |
| author_sort | Bruno Linclau |
| collection | DOAJ |
| description | A large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed. |
| first_indexed | 2024-12-20T01:09:57Z |
| format | Article |
| id | doaj.art-09021fbc5f1b4485b455e2c9674f1fda |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T01:09:57Z |
| publishDate | 2010-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-09021fbc5f1b4485b455e2c9674f1fda2022-12-21T19:58:42ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972010-06-01616210.3762/bjoc.6.621860-5397-6-62Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutaneBruno Linclau0Leo Leung1Jean Nonnenmacher2Graham Tizzard3School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UKSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UKSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UKSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UKA large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed.https://doi.org/10.3762/bjoc.6.62building blockepoxide openinggauche effectorganofluorinevicinal difluoride |
| spellingShingle | Bruno Linclau Leo Leung Jean Nonnenmacher Graham Tizzard Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane Beilstein Journal of Organic Chemistry building block epoxide opening gauche effect organofluorine vicinal difluoride |
| title | Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane |
| title_full | Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane |
| title_fullStr | Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane |
| title_full_unstemmed | Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane |
| title_short | Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane |
| title_sort | synthesis and crystallographic analysis of meso 2 3 difluoro 1 4 butanediol and meso 1 4 dibenzyloxy 2 3 difluorobutane |
| topic | building block epoxide opening gauche effect organofluorine vicinal difluoride |
| url | https://doi.org/10.3762/bjoc.6.62 |
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