{"title":"Fe(NO3)3-9H2O在CF3COOH中氧化2-苯基乙醇：显著的取代基效应","authors":"Zhe Jia, Pu Zhang, Zhi-Xin Guo","doi":"10.1016/j.jorganchem.2024.123288","DOIUrl":null,"url":null,"abstract":"<div><p>2-Phenyl ethanol with various substituents on the phenyl ring was oxidized by Fe(NO<sub>3</sub>)<sub>3</sub>·9H<sub>2</sub>O in the present of trifluoroacetic acid (TFA) at 0°C to room temperature. The product was highly dependent on the electronic properties of the substituent. Weak electron-donating and electron-withdrawing groups (Such as CH<sub>3</sub>, Cl, Br, and F) afforded good to excellent yields (95 – 64 %) of the corresponding phenylacetic acids. Moderate electron-withdrawing groups (Such as CF<sub>3</sub>, COOH) resulted in ∼ 50 % yield of the corresponding phenylacetic acids. However, strong electron-withdrawing group (such as NO<sub>2</sub> and CN) hindered the reaction, the corresponding phenethyl trifluoroacetate was acquired almost quantitatively. Furthermore, the strong electron-donating group of methoxy highly promoted the oxidation, resulted in nitrated benzaldehydes and benzoic acids in relative low yields.</p></div>","PeriodicalId":374,"journal":{"name":"Journal of Organometallic Chemistry","volume":"1018 ","pages":"Article 123288"},"PeriodicalIF":2.1000,"publicationDate":"2024-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"The oxidation of 2-phenyl ethanols by Fe(NO3)3·9H2O in CF3COOH: The dramatic substituent effect\",\"authors\":\"Zhe Jia, Pu Zhang, Zhi-Xin Guo\",\"doi\":\"10.1016/j.jorganchem.2024.123288\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>2-Phenyl ethanol with various substituents on the phenyl ring was oxidized by Fe(NO<sub>3</sub>)<sub>3</sub>·9H<sub>2</sub>O in the present of trifluoroacetic acid (TFA) at 0°C to room temperature. The product was highly dependent on the electronic properties of the substituent. Weak electron-donating and electron-withdrawing groups (Such as CH<sub>3</sub>, Cl, Br, and F) afforded good to excellent yields (95 – 64 %) of the corresponding phenylacetic acids. Moderate electron-withdrawing groups (Such as CF<sub>3</sub>, COOH) resulted in ∼ 50 % yield of the corresponding phenylacetic acids. However, strong electron-withdrawing group (such as NO<sub>2</sub> and CN) hindered the reaction, the corresponding phenethyl trifluoroacetate was acquired almost quantitatively. Furthermore, the strong electron-donating group of methoxy highly promoted the oxidation, resulted in nitrated benzaldehydes and benzoic acids in relative low yields.</p></div>\",\"PeriodicalId\":374,\"journal\":{\"name\":\"Journal of Organometallic Chemistry\",\"volume\":\"1018 \",\"pages\":\"Article 123288\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-07-31\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Organometallic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0022328X24002833\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organometallic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022328X24002833","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
The oxidation of 2-phenyl ethanols by Fe(NO3)3·9H2O in CF3COOH: The dramatic substituent effect
2-Phenyl ethanol with various substituents on the phenyl ring was oxidized by Fe(NO3)3·9H2O in the present of trifluoroacetic acid (TFA) at 0°C to room temperature. The product was highly dependent on the electronic properties of the substituent. Weak electron-donating and electron-withdrawing groups (Such as CH3, Cl, Br, and F) afforded good to excellent yields (95 – 64 %) of the corresponding phenylacetic acids. Moderate electron-withdrawing groups (Such as CF3, COOH) resulted in ∼ 50 % yield of the corresponding phenylacetic acids. However, strong electron-withdrawing group (such as NO2 and CN) hindered the reaction, the corresponding phenethyl trifluoroacetate was acquired almost quantitatively. Furthermore, the strong electron-donating group of methoxy highly promoted the oxidation, resulted in nitrated benzaldehydes and benzoic acids in relative low yields.
期刊介绍：
The Journal of Organometallic Chemistry targets original papers dealing with theoretical aspects, structural chemistry, synthesis, physical and chemical properties (including reaction mechanisms), and practical applications of organometallic compounds.
Organometallic compounds are defined as compounds that contain metal - carbon bonds. The term metal includes all alkali and alkaline earth metals, all transition metals and the lanthanides and actinides in the Periodic Table. Metalloids including the elements in Group 13 and the heavier members of the Groups 14 - 16 are also included. The term chemistry includes syntheses, characterizations and reaction chemistry of all such compounds. Research reports based on use of organometallic complexes in bioorganometallic chemistry, medicine, material sciences, homogeneous catalysis and energy conversion are also welcome.
The scope of the journal has been enlarged to encompass important research on organometallic complexes in bioorganometallic chemistry and material sciences, and of heavier main group elements in organometallic chemistry. The journal also publishes review articles, short communications and notes.
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