Nucleophile-Dependent Regioselective Reaction of (S)‑4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines
Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exc...
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| Veröffentlicht in: | Journal of organic chemistry 2013-05, Vol.78 (9), p.4261-4269 |
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| container_issue | 9 |
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| container_title | Journal of organic chemistry |
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| creator | Jiang, Haizhen Yan, Liuming Xu, Minjun Lu, Wenjun Cai, Yeshan Wan, Wen Yao, Jianhua Wu, Shaoxiong Zhu, Shizheng Hao, Jian |
| description | Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (SRN1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the CN bond. |
| doi_str_mv | 10.1021/jo400073d |
| format | Article |
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The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (SRN1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the CN bond.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo400073d</identifier><identifier>PMID: 23570332</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Benzyl Compounds - chemical synthesis ; Benzyl Compounds - chemistry ; Hydrocarbons, Fluorinated - chemical synthesis ; Hydrocarbons, Fluorinated - chemistry ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Molecular Structure ; Oxazoles - chemical synthesis ; Oxazoles - chemistry ; X-Ray Diffraction</subject><ispartof>Journal of organic chemistry, 2013-05, Vol.78 (9), p.4261-4269</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-314f0122834a08ae63cc99fcc90042558e7ed81174b0d8cfbaa451fd7e62db063</citedby><cites>FETCH-LOGICAL-a315t-314f0122834a08ae63cc99fcc90042558e7ed81174b0d8cfbaa451fd7e62db063</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo400073d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo400073d$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23570332$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jiang, Haizhen</creatorcontrib><creatorcontrib>Yan, Liuming</creatorcontrib><creatorcontrib>Xu, Minjun</creatorcontrib><creatorcontrib>Lu, Wenjun</creatorcontrib><creatorcontrib>Cai, Yeshan</creatorcontrib><creatorcontrib>Wan, Wen</creatorcontrib><creatorcontrib>Yao, Jianhua</creatorcontrib><creatorcontrib>Wu, Shaoxiong</creatorcontrib><creatorcontrib>Zhu, Shizheng</creatorcontrib><creatorcontrib>Hao, Jian</creatorcontrib><title>Nucleophile-Dependent Regioselective Reaction of (S)‑4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (SRN1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the CN bond.</description><subject>Benzyl Compounds - chemical synthesis</subject><subject>Benzyl Compounds - chemistry</subject><subject>Hydrocarbons, Fluorinated - chemical synthesis</subject><subject>Hydrocarbons, Fluorinated - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - chemistry</subject><subject>X-Ray Diffraction</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1Kw0AUhQdRbK0ufAHpRmjB0Tt_SbrUalUoFvzZCWGa3GjqNBMzidiufAVf0SdxpNWVm3vvge8eOIeQfQbHDDg7mVkJAKFIN0ibKQ40GIDcJG0AzqnggWiRHedmngGl1DZpcaFCEIK3yeNNkxi05XNukJ5jiUWKRd29xafcOjSY1Pkbeqn9YYuuzbq9u_7Xx6ekZ1gsF4ZyOjKNraw2L16xI0En73ppTV6g2yVbmTYO99a7Qx5GF_fDKzqeXF4PT8dUC6ZqKpjMgHEeCakh0hiIJBkMMj8AJFcqwhDTiLFQTiGNkmyqtVQsS0MMeDqFQHRIb-VbVva1QVfH89wlaIwu0DYuZkJGCoQUwqP9FZpU1rkKs7is8rmuFjGD-KfM-K9Mzx6sbZvpHNM_8rc9DxyuAJ04_9dUhU_5j9E33FN6yw</recordid><startdate>20130503</startdate><enddate>20130503</enddate><creator>Jiang, Haizhen</creator><creator>Yan, Liuming</creator><creator>Xu, Minjun</creator><creator>Lu, Wenjun</creator><creator>Cai, Yeshan</creator><creator>Wan, Wen</creator><creator>Yao, Jianhua</creator><creator>Wu, Shaoxiong</creator><creator>Zhu, Shizheng</creator><creator>Hao, Jian</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130503</creationdate><title>Nucleophile-Dependent Regioselective Reaction of (S)‑4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines</title><author>Jiang, Haizhen ; Yan, Liuming ; Xu, Minjun ; Lu, Wenjun ; Cai, Yeshan ; Wan, Wen ; Yao, Jianhua ; Wu, Shaoxiong ; Zhu, Shizheng ; Hao, Jian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-314f0122834a08ae63cc99fcc90042558e7ed81174b0d8cfbaa451fd7e62db063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Benzyl Compounds - chemical synthesis</topic><topic>Benzyl Compounds - chemistry</topic><topic>Hydrocarbons, Fluorinated - chemical synthesis</topic><topic>Hydrocarbons, Fluorinated - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - chemistry</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jiang, Haizhen</creatorcontrib><creatorcontrib>Yan, Liuming</creatorcontrib><creatorcontrib>Xu, Minjun</creatorcontrib><creatorcontrib>Lu, Wenjun</creatorcontrib><creatorcontrib>Cai, Yeshan</creatorcontrib><creatorcontrib>Wan, Wen</creatorcontrib><creatorcontrib>Yao, Jianhua</creatorcontrib><creatorcontrib>Wu, Shaoxiong</creatorcontrib><creatorcontrib>Zhu, Shizheng</creatorcontrib><creatorcontrib>Hao, Jian</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jiang, Haizhen</au><au>Yan, Liuming</au><au>Xu, Minjun</au><au>Lu, Wenjun</au><au>Cai, Yeshan</au><au>Wan, Wen</au><au>Yao, Jianhua</au><au>Wu, Shaoxiong</au><au>Zhu, Shizheng</au><au>Hao, Jian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nucleophile-Dependent Regioselective Reaction of (S)‑4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2013-05-03</date><risdate>2013</risdate><volume>78</volume><issue>9</issue><spage>4261</spage><epage>4269</epage><pages>4261-4269</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (SRN1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the CN bond.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23570332</pmid><doi>10.1021/jo400073d</doi><tpages>9</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Benzyl Compounds - chemical synthesis Benzyl Compounds - chemistry Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Oxazoles - chemical synthesis Oxazoles - chemistry X-Ray Diffraction |
| title | Nucleophile-Dependent Regioselective Reaction of (S)‑4-Benzyl-2-Fluoroalkyl-1,3-Oxazolines |
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