Synthesis of gem-difluorocyclopentane/hexane building blocks
Synthesis of gem-difluorocycloalkane building blocks is described. [Display omitted] •An approach to gem-difluorocyclopentane/hexane carboxylic acids and amines is developed.•Straightforward fluorination of 3-ketocycloalkanecarboxylates leads to the target 3,3-difluoro-substitited cycloalkanes.•For...
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| Veröffentlicht in: | Journal of fluorine chemistry 2017-07, Vol.199, p.60-66 |
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| container_title | Journal of fluorine chemistry |
| container_volume | 199 |
| creator | Melnykov, Kostiantyn P. Nosik, Pavel S. Kurpil, Bohdan B. Sibgatulin, Dmitriy A. Volochnyuk, Dmitriy M. Ryabukhin, Sergey V. Grygorenko, Oleksandr O. |
| description | Synthesis of gem-difluorocycloalkane building blocks is described.
[Display omitted]
•An approach to gem-difluorocyclopentane/hexane carboxylic acids and amines is developed.•Straightforward fluorination of 3-ketocycloalkanecarboxylates leads to the target 3,3-difluoro-substitited cycloalkanes.•For the 2,2-difluorocycloalkanecarboxylic acids, the bypass route via (2-oxocycloalkyl)methyl acetates is necessary.•2,2-Difluorocycloalkylamines can be obtained via deoxofluorination of 2-(trifluoroacetylamino)cycloalkanones.
An approach to the preparation of gem-difluorocyclopentane/hexane-derived carboxylic acids and amines is described. Whereas for 3,3-difluoro-substituted cycloalkanones, straightforward deoxofluorination of the corresponding ketoesters led to the target compounds, in the case of 2,2-difluoro isomers, the bypass or alternative routes were necessary. |
| doi_str_mv | 10.1016/j.jfluchem.2017.04.012 |
| format | Article |
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[Display omitted]
•An approach to gem-difluorocyclopentane/hexane carboxylic acids and amines is developed.•Straightforward fluorination of 3-ketocycloalkanecarboxylates leads to the target 3,3-difluoro-substitited cycloalkanes.•For the 2,2-difluorocycloalkanecarboxylic acids, the bypass route via (2-oxocycloalkyl)methyl acetates is necessary.•2,2-Difluorocycloalkylamines can be obtained via deoxofluorination of 2-(trifluoroacetylamino)cycloalkanones.
An approach to the preparation of gem-difluorocyclopentane/hexane-derived carboxylic acids and amines is described. Whereas for 3,3-difluoro-substituted cycloalkanones, straightforward deoxofluorination of the corresponding ketoesters led to the target compounds, in the case of 2,2-difluoro isomers, the bypass or alternative routes were necessary.</description><identifier>ISSN: 0022-1139</identifier><identifier>EISSN: 1873-3328</identifier><identifier>DOI: 10.1016/j.jfluchem.2017.04.012</identifier><language>eng</language><publisher>Lausanne: Elsevier B.V</publisher><subject>Acids ; Amines ; Carboxylic acids ; Chemical synthesis ; Conformational restriction ; Cycloalkanes ; DAST ; Fluorination ; Fluorine ; Isomers ; Ketoesters ; Organofluorine compounds ; Studies ; Xtal-Fluor</subject><ispartof>Journal of fluorine chemistry, 2017-07, Vol.199, p.60-66</ispartof><rights>2017 Elsevier B.V.</rights><rights>Copyright Elsevier BV Jul 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c340t-924fd5f21d68a09fab636b593135c5d8fec973ebaafa1f69660e3b9d74659f923</citedby><cites>FETCH-LOGICAL-c340t-924fd5f21d68a09fab636b593135c5d8fec973ebaafa1f69660e3b9d74659f923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jfluchem.2017.04.012$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Melnykov, Kostiantyn P.</creatorcontrib><creatorcontrib>Nosik, Pavel S.</creatorcontrib><creatorcontrib>Kurpil, Bohdan B.</creatorcontrib><creatorcontrib>Sibgatulin, Dmitriy A.</creatorcontrib><creatorcontrib>Volochnyuk, Dmitriy M.</creatorcontrib><creatorcontrib>Ryabukhin, Sergey V.</creatorcontrib><creatorcontrib>Grygorenko, Oleksandr O.</creatorcontrib><title>Synthesis of gem-difluorocyclopentane/hexane building blocks</title><title>Journal of fluorine chemistry</title><description>Synthesis of gem-difluorocycloalkane building blocks is described.
[Display omitted]
•An approach to gem-difluorocyclopentane/hexane carboxylic acids and amines is developed.•Straightforward fluorination of 3-ketocycloalkanecarboxylates leads to the target 3,3-difluoro-substitited cycloalkanes.•For the 2,2-difluorocycloalkanecarboxylic acids, the bypass route via (2-oxocycloalkyl)methyl acetates is necessary.•2,2-Difluorocycloalkylamines can be obtained via deoxofluorination of 2-(trifluoroacetylamino)cycloalkanones.
An approach to the preparation of gem-difluorocyclopentane/hexane-derived carboxylic acids and amines is described. Whereas for 3,3-difluoro-substituted cycloalkanones, straightforward deoxofluorination of the corresponding ketoesters led to the target compounds, in the case of 2,2-difluoro isomers, the bypass or alternative routes were necessary.</description><subject>Acids</subject><subject>Amines</subject><subject>Carboxylic acids</subject><subject>Chemical synthesis</subject><subject>Conformational restriction</subject><subject>Cycloalkanes</subject><subject>DAST</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Isomers</subject><subject>Ketoesters</subject><subject>Organofluorine compounds</subject><subject>Studies</subject><subject>Xtal-Fluor</subject><issn>0022-1139</issn><issn>1873-3328</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LxDAURYMoOI7-BSm4bucladMGXCiDXzDgQl2HNH2ZSe00Y9KK8--tjK5d3c295_EOIZcUMgpULNqstd1oNrjNGNAygzwDyo7IjFYlTzln1TGZATCWUsrlKTmLsQWAEspqRq5f9v2wwehi4m2yxm3auInmgzd70_kd9oPucbHBrymSenRd4_p1UnfevMdzcmJ1F_HiN-fk7f7udfmYrp4fnpa3q9TwHIZUstw2hWW0EZUGaXUtuKgLySkvTNFUFo0sOdZaW02tkEIA8lo2ZS4KaSXjc3J14O6C_xgxDqr1Y-ink4pKXubAciamlji0TPAxBrRqF9xWh72ioH5MqVb9mVI_phTkajI1DW8OQ5x--HQYVDQOe4ONC2gG1Xj3H-Ibgbd1og</recordid><startdate>201707</startdate><enddate>201707</enddate><creator>Melnykov, Kostiantyn P.</creator><creator>Nosik, Pavel S.</creator><creator>Kurpil, Bohdan B.</creator><creator>Sibgatulin, Dmitriy A.</creator><creator>Volochnyuk, Dmitriy M.</creator><creator>Ryabukhin, Sergey V.</creator><creator>Grygorenko, Oleksandr O.</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope></search><sort><creationdate>201707</creationdate><title>Synthesis of gem-difluorocyclopentane/hexane building blocks</title><author>Melnykov, Kostiantyn P. ; Nosik, Pavel S. ; Kurpil, Bohdan B. ; Sibgatulin, Dmitriy A. ; Volochnyuk, Dmitriy M. ; Ryabukhin, Sergey V. ; Grygorenko, Oleksandr O.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c340t-924fd5f21d68a09fab636b593135c5d8fec973ebaafa1f69660e3b9d74659f923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acids</topic><topic>Amines</topic><topic>Carboxylic acids</topic><topic>Chemical synthesis</topic><topic>Conformational restriction</topic><topic>Cycloalkanes</topic><topic>DAST</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Isomers</topic><topic>Ketoesters</topic><topic>Organofluorine compounds</topic><topic>Studies</topic><topic>Xtal-Fluor</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Melnykov, Kostiantyn P.</creatorcontrib><creatorcontrib>Nosik, Pavel S.</creatorcontrib><creatorcontrib>Kurpil, Bohdan B.</creatorcontrib><creatorcontrib>Sibgatulin, Dmitriy A.</creatorcontrib><creatorcontrib>Volochnyuk, Dmitriy M.</creatorcontrib><creatorcontrib>Ryabukhin, Sergey V.</creatorcontrib><creatorcontrib>Grygorenko, Oleksandr O.</creatorcontrib><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of fluorine chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Melnykov, Kostiantyn P.</au><au>Nosik, Pavel S.</au><au>Kurpil, Bohdan B.</au><au>Sibgatulin, Dmitriy A.</au><au>Volochnyuk, Dmitriy M.</au><au>Ryabukhin, Sergey V.</au><au>Grygorenko, Oleksandr O.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of gem-difluorocyclopentane/hexane building blocks</atitle><jtitle>Journal of fluorine chemistry</jtitle><date>2017-07</date><risdate>2017</risdate><volume>199</volume><spage>60</spage><epage>66</epage><pages>60-66</pages><issn>0022-1139</issn><eissn>1873-3328</eissn><abstract>Synthesis of gem-difluorocycloalkane building blocks is described.
[Display omitted]
•An approach to gem-difluorocyclopentane/hexane carboxylic acids and amines is developed.•Straightforward fluorination of 3-ketocycloalkanecarboxylates leads to the target 3,3-difluoro-substitited cycloalkanes.•For the 2,2-difluorocycloalkanecarboxylic acids, the bypass route via (2-oxocycloalkyl)methyl acetates is necessary.•2,2-Difluorocycloalkylamines can be obtained via deoxofluorination of 2-(trifluoroacetylamino)cycloalkanones.
An approach to the preparation of gem-difluorocyclopentane/hexane-derived carboxylic acids and amines is described. Whereas for 3,3-difluoro-substituted cycloalkanones, straightforward deoxofluorination of the corresponding ketoesters led to the target compounds, in the case of 2,2-difluoro isomers, the bypass or alternative routes were necessary.</abstract><cop>Lausanne</cop><pub>Elsevier B.V</pub><doi>10.1016/j.jfluchem.2017.04.012</doi><tpages>7</tpages></addata></record> |
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| subjects | Acids Amines Carboxylic acids Chemical synthesis Conformational restriction Cycloalkanes DAST Fluorination Fluorine Isomers Ketoesters Organofluorine compounds Studies Xtal-Fluor |
| title | Synthesis of gem-difluorocyclopentane/hexane building blocks |
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