File Download
There are no files associated with this item.
Links for fulltext
(May Require Subscription)
- Publisher Website: 10.1021/jo000458j
- Scopus: eid_2-s2.0-0034733112
- WOS: WOS:000087925800035
- Find via
Supplementary
- Citations:
- Appears in Collections:
Article: Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ
Title | Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ |
---|---|
Authors | |
Issue Date | 2000 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | Journal Of Organic Chemistry, 2000, v. 65 n. 13, p. 4179-4184 How to Cite? |
Abstract | A novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Oxone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF 3COOMe, and CH 2Cl, were attached to phenols, anisoles, or aryl rings via a C 2 or C 3 methylene linker. In a homogeneous solvent system of CH 3CN and H 2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation. |
Persistent Identifier | http://hdl.handle.net/10722/69240 |
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 | Wong, MK | en_HK |
dc.contributor.author | Yan, Z | en_HK |
dc.date.accessioned | 2010-09-06T06:11:51Z | - |
dc.date.available | 2010-09-06T06:11:51Z | - |
dc.date.issued | 2000 | en_HK |
dc.identifier.citation | Journal Of Organic Chemistry, 2000, v. 65 n. 13, p. 4179-4184 | en_HK |
dc.identifier.issn | 0022-3263 | en_HK |
dc.identifier.uri | http://hdl.handle.net/10722/69240 | - |
dc.description.abstract | A novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Oxone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF 3COOMe, and CH 2Cl, were attached to phenols, anisoles, or aryl rings via a C 2 or C 3 methylene linker. In a homogeneous solvent system of CH 3CN and H 2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation. | 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 | Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ | en_HK |
dc.type | Article | en_HK |
dc.identifier.openurl | http://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0022-3263&volume=65&spage=4179&epage=4184&date=2000&atitle=Regioselective+intramolecular+oxidation+of+phenols+and+anisoles+by+dioxiranes+generated+in+situ | 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/jo000458j | en_HK |
dc.identifier.scopus | eid_2-s2.0-0034733112 | en_HK |
dc.identifier.hkuros | 50328 | en_HK |
dc.relation.references | http://www.scopus.com/mlt/select.url?eid=2-s2.0-0034733112&selection=ref&src=s&origin=recordpage | en_HK |
dc.identifier.volume | 65 | en_HK |
dc.identifier.issue | 13 | en_HK |
dc.identifier.spage | 4179 | en_HK |
dc.identifier.epage | 4184 | en_HK |
dc.identifier.isi | WOS:000087925800035 | - |
dc.publisher.place | United States | en_HK |
dc.identifier.scopusauthorid | Yang, D=7404800756 | en_HK |
dc.identifier.scopusauthorid | Wong, MK=37105480700 | en_HK |
dc.identifier.scopusauthorid | Yan, Z=7402519416 | en_HK |
dc.identifier.issnl | 0022-3263 | - |