Mechanistic investigations in α‐hydroxycarbonyls reduction by BH 4 ‐
dc.contributor.author | Marincean, Simona | en_US |
dc.contributor.author | Fritz, Michael | en_US |
dc.contributor.author | Scamp, Ryan | en_US |
dc.contributor.author | Jackson, James E. | en_US |
dc.date.accessioned | 2013-02-12T19:01:08Z | |
dc.date.available | 2014-02-03T16:21:45Z | en_US |
dc.date.issued | 2012-12 | en_US |
dc.identifier.citation | Marincean, 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.issn | 0894-3230 | en_US |
dc.identifier.issn | 1099-1395 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/96374 | |
dc.publisher | Gaussian, Inc. | en_US |
dc.publisher | Wiley Periodicals, Inc. | en_US |
dc.subject.other | Rate | en_US |
dc.subject.other | Activation | en_US |
dc.subject.other | Carbonyl | en_US |
dc.subject.other | Dihydrogen Bonding | en_US |
dc.title | Mechanistic investigations in α‐hydroxycarbonyls reduction by BH 4 ‐ | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/96374/1/poc2986.pdf | |
dc.identifier.doi | 10.1002/poc.2986 | en_US |
dc.identifier.source | Journal of Physical Organic Chemistry | en_US |
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dc.identifier.citedreference | The 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 |
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dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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