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Article: Novel cyclic ketones for catalytic oxidation reactions
Title | Novel cyclic ketones for catalytic oxidation reactions |
---|---|
Authors | |
Issue Date | 1998 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | Journal Of Organic Chemistry, 1998, v. 63 n. 26, p. 9888-9894 How to Cite? |
Abstract | In our effort to search for C2 symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11- membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%). |
Persistent Identifier | http://hdl.handle.net/10722/68774 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID | |
References |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Yang, D | en_HK |
dc.contributor.author | Yip, YC | en_HK |
dc.contributor.author | Tang, MW | en_HK |
dc.contributor.author | Wong, MK | en_HK |
dc.contributor.author | Cheung, KK | en_HK |
dc.date.accessioned | 2010-09-06T06:07:36Z | - |
dc.date.available | 2010-09-06T06:07:36Z | - |
dc.date.issued | 1998 | en_HK |
dc.identifier.citation | Journal Of Organic Chemistry, 1998, v. 63 n. 26, p. 9888-9894 | en_HK |
dc.identifier.issn | 0022-3263 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/68774 | - |
dc.description.abstract | In our effort to search for C2 symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11- membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%). | en_HK |
dc.language | eng | en_HK |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | en_HK |
dc.relation.ispartof | Journal of Organic Chemistry | en_HK |
dc.title | Novel cyclic ketones for catalytic oxidation reactions | en_HK |
dc.type | Article | en_HK |
dc.identifier.openurl | http://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=63&issue=26&spage=9888&epage=9894&date=1998&atitle=Novel+cyclic+ketones+for+catalytic+oxidation+reactions | en_HK |
dc.identifier.email | Yang, D:yangdan@hku.hk | en_HK |
dc.identifier.authority | Yang, D=rp00825 | en_HK |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jo981659e | en_HK |
dc.identifier.scopus | eid_2-s2.0-0032567328 | en_HK |
dc.identifier.hkuros | 40136 | en_HK |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0032567328&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 63 | en_HK |
dc.identifier.issue | 26 | en_HK |
dc.identifier.spage | 9888 | en_HK |
dc.identifier.epage | 9894 | en_HK |
dc.identifier.isi | WOS:000077834800049 | - |
dc.publisher.place | United States | en_HK |
dc.identifier.scopusauthorid | Yang, D=7404800756 | en_HK |
dc.identifier.scopusauthorid | Yip, YC=7005596386 | en_HK |
dc.identifier.scopusauthorid | Tang, MW=7401974042 | en_HK |
dc.identifier.scopusauthorid | Wong, MK=7403908449 | en_HK |
dc.identifier.scopusauthorid | Cheung, KK=7402406613 | en_HK |
dc.identifier.issnl | 0022-3263 | - |