Mechanistic Studies on the Roles of the Oxidant and Hydrogen Bonding in Determining the Selectivity in Alkene Oxidation in the Presence of Molybdenum Catalysts
When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert‐butyl hydroperoxide (TBHP, 5.5 M) in dodecane is used as the oxidant for the oxi...
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| Published in | Chemistry : a European journal Vol. 19; no. 6; pp. 2030 - 2040 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
04.02.2013
WILEY‐VCH Verlag Wiley Subscription Services, Inc |
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| Abstract | When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert‐butyl hydroperoxide (TBHP, 5.5 M) in dodecane is used as the oxidant for the oxidation of cyclohexene, cyclohexene oxide is formed with high selectivity. However, when H2O2 is used as the oxidant, the corresponding cis‐1,2‐diol is formed as the major product. Calculations performed by using density functional theory revealed the nature of the different competing mechanisms operating during the catalysis process and also provided an insight into the influence of the oxidant and hydrogen bonding on the catalysis process. The mechanistic investigations can therefore serve as a guide in the design of molybdenum‐based catalysts for the oxidation of olefins.
Molybdenum‐catalysed oxidation: Calculations performed by using density functional theory indicate that different mechanisms compete during the homogeneous catalysis of olefin oxidation carried out in the presence of molybdenum‐based catalysts (see scheme). |
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| AbstractList | When the molybdenum oxo(peroxo) acetylide complex [CpMo(O-O)(O)C≡CPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert-butyl hydroperoxide (TBHP, 5.5 M) in dodecane is used as the oxidant for the oxidation of cyclohexene, cyclohexene oxide is formed with high selectivity. However, when H(2)O(2) is used as the oxidant, the corresponding cis-1,2-diol is formed as the major product. Calculations performed by using density functional theory revealed the nature of the different competing mechanisms operating during the catalysis process and also provided an insight into the influence of the oxidant and hydrogen bonding on the catalysis process. The mechanistic investigations can therefore serve as a guide in the design of molybdenum-based catalysts for the oxidation of olefins. When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert‐butyl hydroperoxide (TBHP, 5.5 M) in dodecane is used as the oxidant for the oxidation of cyclohexene, cyclohexene oxide is formed with high selectivity. However, when H2O2 is used as the oxidant, the corresponding cis‐1,2‐diol is formed as the major product. Calculations performed by using density functional theory revealed the nature of the different competing mechanisms operating during the catalysis process and also provided an insight into the influence of the oxidant and hydrogen bonding on the catalysis process. The mechanistic investigations can therefore serve as a guide in the design of molybdenum‐based catalysts for the oxidation of olefins. Molybdenum‐catalysed oxidation: Calculations performed by using density functional theory indicate that different mechanisms compete during the homogeneous catalysis of olefin oxidation carried out in the presence of molybdenum‐based catalysts (see scheme). Abstract When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert ‐butyl hydroperoxide (TBHP, 5.5 M ) in dodecane is used as the oxidant for the oxidation of cyclohexene, cyclohexene oxide is formed with high selectivity. However, when H 2 O 2 is used as the oxidant, the corresponding cis ‐1,2‐diol is formed as the major product. Calculations performed by using density functional theory revealed the nature of the different competing mechanisms operating during the catalysis process and also provided an insight into the influence of the oxidant and hydrogen bonding on the catalysis process. The mechanistic investigations can therefore serve as a guide in the design of molybdenum‐based catalysts for the oxidation of olefins. When the molybdenum oxo(peroxo) acetylide complex [CpMo(O-O)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert-butyl hydroperoxide (TBHP, 5.5M) in dodecane is used as the oxidant for the oxidation of cyclohexene, cyclohexene oxide is formed with high selectivity. However, when H sub(2)O sub(2) is used as the oxidant, the corresponding cis-1,2-diol is formed as the major product. Calculations performed by using density functional theory revealed the nature of the different competing mechanisms operating during the catalysis process and also provided an insight into the influence of the oxidant and hydrogen bonding on the catalysis process. The mechanistic investigations can therefore serve as a guide in the design of molybdenum-based catalysts for the oxidation of olefins. Molybdenum-catalysed oxidation: Calculations performed by using density functional theory indicate that different mechanisms compete during the homogeneous catalysis of olefin oxidation carried out in the presence of molybdenum-based catalysts (see scheme). When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product selectivity is obtained depending on the oxidant employed. When tert-butyl hydroperoxide (TBHP, 5.5M) in dodecane is used as the oxidant for the oxidation of cyclohexene, cyclohexene oxide is formed with high selectivity. However, when H2O2 is used as the oxidant, the corresponding cis-1,2-diol is formed as the major product. Calculations performed by using density functional theory revealed the nature of the different competing mechanisms operating during the catalysis process and also provided an insight into the influence of the oxidant and hydrogen bonding on the catalysis process. The mechanistic investigations can therefore serve as a guide in the design of molybdenum-based catalysts for the oxidation of olefins. [PUBLICATION ABSTRACT] |
| Author | Vanka, Kumar Umbarkar, Shubhangi B. Chandra, Prakash Pandhare, Swati L. Dongare, Mohan K. |
| Author_xml | – sequence: 1 givenname: Prakash surname: Chandra fullname: Chandra, Prakash organization: CSIR-NCL Catalysis and Inorganic Chemistry Division, Dr. Homi Bhabha Road. Pashan, Pune, Maharastra (India) – sequence: 2 givenname: Swati L. surname: Pandhare fullname: Pandhare, Swati L. organization: CSIR-NCL Catalysis and Inorganic Chemistry Division, Dr. Homi Bhabha Road. Pashan, Pune, Maharastra (India) – sequence: 3 givenname: Shubhangi B. surname: Umbarkar fullname: Umbarkar, Shubhangi B. email: sb.umbarkar@ncl.res.in organization: CSIR-NCL Catalysis and Inorganic Chemistry Division, Dr. Homi Bhabha Road. Pashan, Pune, Maharastra (India) – sequence: 4 givenname: Mohan K. surname: Dongare fullname: Dongare, Mohan K. email: mk.dongare@ncl.res.in organization: CSIR-NCL Catalysis and Inorganic Chemistry Division, Dr. Homi Bhabha Road. Pashan, Pune, Maharastra (India) – sequence: 5 givenname: Kumar surname: Vanka fullname: Vanka, Kumar email: k.vanka@ncl.res.in organization: Physical Chemistry Division CSIR-NCL, Dr. Homi Bhabha Road, Pashan, Pune, Maharashtra (India), Fax: (+20) 2590-2636 |
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| Snippet | When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product... When the molybdenum oxo(peroxo) acetylide complex [CpMo(O-O)(O)C≡CPh] is used as a catalyst for the oxidation of olefins, completely different product... Abstract When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product... When the molybdenum oxo(peroxo) acetylide complex [CpMo(OO)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product... When the molybdenum oxo(peroxo) acetylide complex [CpMo(O-O)(O)CCPh] is used as a catalyst for the oxidation of olefins, completely different product... |
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| SubjectTerms | Alkenes - chemistry Catalysis Catalysts Chemistry Coordination Complexes - chemistry Cyclohexenes - chemistry epoxides homogeneous catalysis Hydrogen Bonding Models, Molecular Molybdenum Molybdenum - chemistry Olefins Oxidants Oxidation Oxidation-Reduction Oxidizing agents Selectivity tert-Butylhydroperoxide - chemistry |
| Title | Mechanistic Studies on the Roles of the Oxidant and Hydrogen Bonding in Determining the Selectivity in Alkene Oxidation in the Presence of Molybdenum Catalysts |
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