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Mechanistic investigations in α‐hydroxycarbonyls reduction by BH 4 ‐

dc.contributor.authorMarincean, Simonaen_US
dc.contributor.authorFritz, Michaelen_US
dc.contributor.authorScamp, Ryanen_US
dc.contributor.authorJackson, James E.en_US
dc.date.accessioned2013-02-12T19:01:08Z
dc.date.available2014-02-03T16:21:45Zen_US
dc.date.issued2012-12en_US
dc.identifier.citationMarincean, Simona; Fritz, Michael; Scamp, Ryan; Jackson, James E. (2012). "Mechanistic investigations in α‐hydroxycarbonyls reduction by BH 4 ‐ ." Journal of Physical Organic Chemistry (12): 1186-1192. <http://hdl.handle.net/2027.42/96374>en_US
dc.identifier.issn0894-3230en_US
dc.identifier.issn1099-1395en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/96374
dc.publisherGaussian, Inc.en_US
dc.publisherWiley Periodicals, Inc.en_US
dc.subject.otherRateen_US
dc.subject.otherActivationen_US
dc.subject.otherCarbonylen_US
dc.subject.otherDihydrogen Bondingen_US
dc.titleMechanistic investigations in α‐hydroxycarbonyls reduction by BH 4 ‐en_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.description.peerreviewedPeer Revieweden_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/96374/1/poc2986.pdf
dc.identifier.doi10.1002/poc.2986en_US
dc.identifier.sourceJournal of Physical Organic Chemistryen_US
dc.identifier.citedreferenceJ. V. Pothuluri, J. P. Freeman, F. E. Evans, C. E. Cerniglia, Appl. Environ. Microbiol. 1992, 58, 3654.en_US
dc.identifier.citedreferenceW. N. O. Wylie, A. J. Lough, R. H. Morris, Organometallics 2012, 31, 2137.en_US
dc.identifier.citedreferenceA. Merz, F. Dietl, R. Tomahogh, G. Weber, G. M. Sheldrick, Tetrahedron 1984, 40, 665.en_US
dc.identifier.citedreferenceM. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2010.en_US
dc.identifier.citedreferenceThe procedure employed by Gatling and Jackson involved hydrolysis via treatment with H 2 O 2 followed by NaOH and subsequent derivatization of the diol products to obtain the corresponding silyl derivatives that were analyzed by gas chromatography. While our own experiments reproduced the trans:cis ratio, the carbon balance was low due to the high stability of the alkoxyborate species corresponding to the cis diol. However for our studies, hydrolysis was achieved via treatment with H 2 SO 4. The exothermicity of the reaction led to complete removal of the reaction solvent, dichloromethane, thus ensuring that all species were in an aqueous solution that was analyzed subsequently by HPLC. Removal of borate salts was achieved by treatment with a methanolic solution of HCl. The carbon balance for the latter method showed that all products were hydrolyzed and there was no starting ketone present.en_US
dc.identifier.citedreferenceC. Y. Legault, CYLview, 1.0b, Université de Sherbrooke, 2009. ( http://www.cylview.org )en_US
dc.identifier.citedreferenceM. Cossi, N. Rega, G. Scalmani, V. Barone, J. Comp. Chem. 2003, 24, 669.en_US
dc.identifier.citedreferenceV. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995.en_US
dc.identifier.citedreferenceM. J. Frisch, J. A. Pople, J. S. Binkley, J. Chem. Phys. 1984, 80, 3265.en_US
dc.identifier.citedreferenceT. Clark, J. Chandrasekhar, G. W. Spitznagel, P. v. R. Schleyer, J. Comp. Chem. 1983, 4, 294.en_US
dc.identifier.citedreferenceK. Raghavachari, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650.en_US
dc.identifier.citedreferenceA. D. McLean, G. S. Chandler, J. Chem. Phys. 1988, 72, 5639.en_US
dc.identifier.citedreferenceM. Head‐Gordon, T. Head‐Gordon, Chem. Phys. Lett. 1990, 220, 122.en_US
dc.identifier.citedreferenceM. J. Frisch, M. Head‐Gordon, J. A. Pople, Chem. Phys. Lett. 1990, 166, 281.en_US
dc.identifier.citedreferenceM. J. Frisch, M. Head‐Gordon, J. A. Pople, Chem. Phys. Lett. 1990, 166, 275.en_US
dc.identifier.citedreferenceS. Saebø, J. Almlöf, Chem. Phys. Lett. 1989, 154, 83.en_US
dc.identifier.citedreferenceM. Head‐Gordon, J. A. Pople, J. Chem. Phys. 1988, 89, 5777.en_US
dc.identifier.citedreferenceH. I. Schlesinger, H. C. Brown, J. Am. Chem. Soc. 1940, 62, 3429.en_US
dc.identifier.citedreferenceS. W. Chaikin, W. G. Brown, J. Am. Chem. Soc. 1949, 71, 122.en_US
dc.identifier.citedreferenceE. R. Garett, D. A. Lyttle, J. Am. Chem. Soc. 1953, 75, 6051.en_US
dc.identifier.citedreferenceD. C. Wigfield, F. W. Gowland, J. Org. Chem. 1977, 42, 1108.en_US
dc.identifier.citedreferenceD. C. Wigfield, Tetrahedron 1979, 35, 449.en_US
dc.identifier.citedreferenceO. Eisenstein, H. B. Schlegel, M. M. Kayser, J. Org. Chem. 1982, 47, 2886.en_US
dc.identifier.citedreferenceM. M. Kayser, T. B. McMahon, Tetrahedron Lett. 1984, 25, 3379.en_US
dc.identifier.citedreferenceR. S. Glass, D. R. Deardorff, K. Henegar, Tetrahedron Lett. 1980, 21, 2467.en_US
dc.identifier.citedreferenceV. K. Yadav, D. A. Jeyaraj, R. Balamurugan, Tetrahedron 2000, 56, 7581.en_US
dc.identifier.citedreferenceD. J. Raber, W. C. Guida, D. C. Shoenberger, Tetrahedron Lett. 1981, 22, 5107.en_US
dc.identifier.citedreferenceY. Suzuki, D. Kaeneno, S. Tomoda, J. Phys. Chem. A 2009, 113, 2578.en_US
dc.identifier.citedreferenceR. Custelcean, J. E. Jackson, Chem. Rev. 2001, 101, 1963.en_US
dc.identifier.citedreferenceL. M. Epstein, E. S. Shubina, Coord. Chem. Rev. 2002, 231, 165.en_US
dc.identifier.citedreferenceW. K. Fung, X. Huang, M. L. Man, S. M. Ng, M. Y. Hung, Z. Y. Lin, C. P. Lau, J. Am. Chem. Soc. 2003, 125, 11539.en_US
dc.identifier.citedreferenceS. L. Gao, W. Wu, Y. R. Mo, J. Phys. Chem. A 2009, 113, 8108.en_US
dc.identifier.citedreferenceS. Marincean, J. E. Jackson, J. Phys. Chem. A 2004, 108, 5521.en_US
dc.identifier.citedreferenceW. Yao, R. H. Crabtree, Inorg. Chem. 1996, 35, 3070.en_US
dc.identifier.citedreferenceS. C. Gatling, J. E. Jackson, J. Am. Chem. Soc. 1999, 121, 8655.en_US
dc.identifier.citedreferenceC. P. Lau, S. M. Ng, G. C. Jia, Z. Y. Lin, Coord. Chem. Rev. 2007, 251, 2223.en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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