Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes

The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained f...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2019-06, Vol.84 (12), p.8309-8314
Main Authors: Hill, Jarvis, Tam, William
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143
cites cdi_FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143
container_end_page 8314
container_issue 12
container_start_page 8309
container_title Journal of organic chemistry
container_volume 84
creator Hill, Jarvis
Tam, William
description The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C regioisomeric ring-opened products has been proposed.
doi_str_mv 10.1021/acs.joc.9b01094
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2248376098</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2248376098</sourcerecordid><originalsourceid>FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143</originalsourceid><addsrcrecordid>eNo9kD1PwzAQhi0EgvIxs6GMLGnPdpzUI6r4kioVITpHF-cCrhK7xKmg_fUYtXDLO9xzr3QPY9ccxhwEn6AJ45U3Y10BB50dsRFXAtJcQ3bMRgBCpFLk8oydh7CCOEqpU3YmOddCaRix1Qu2LdZ2003m9GVDcmdsncy8wQHb7Y7q5NW693SxJhczeSU0g_UuJL5Jli5su46G3hpsk8U3VuR23vnK9y5WkqOQfNnhI65sR-GSnTTYBro65AVbPty_zZ7S-eLxeXY3T43QxZAqLaa5JgHZFKWqTSMrIlSZLBDqItdYNJUoAEwBOZdVLYhrlKg0GqwNz-QFu933rnv_uaEwlJ0NhuKbjvwmlEJkU1nkoKcRnexR0_sQemrKdW877Lclh_JXcBkFl1FweRAcL24O5Zuqo_qf_zMqfwDWQnnr</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2248376098</pqid></control><display><type>article</type><title>Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Hill, Jarvis ; Tam, William</creator><creatorcontrib>Hill, Jarvis ; Tam, William</creatorcontrib><description>The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C regioisomeric ring-opened products has been proposed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b01094</identifier><identifier>PMID: 31192590</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of organic chemistry, 2019-06, Vol.84 (12), p.8309-8314</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143</citedby><cites>FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143</cites><orcidid>0000-0002-1375-881X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31192590$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hill, Jarvis</creatorcontrib><creatorcontrib>Tam, William</creatorcontrib><title>Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C regioisomeric ring-opened products has been proposed.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNo9kD1PwzAQhi0EgvIxs6GMLGnPdpzUI6r4kioVITpHF-cCrhK7xKmg_fUYtXDLO9xzr3QPY9ccxhwEn6AJ45U3Y10BB50dsRFXAtJcQ3bMRgBCpFLk8oydh7CCOEqpU3YmOddCaRix1Qu2LdZ2003m9GVDcmdsncy8wQHb7Y7q5NW693SxJhczeSU0g_UuJL5Jli5su46G3hpsk8U3VuR23vnK9y5WkqOQfNnhI65sR-GSnTTYBro65AVbPty_zZ7S-eLxeXY3T43QxZAqLaa5JgHZFKWqTSMrIlSZLBDqItdYNJUoAEwBOZdVLYhrlKg0GqwNz-QFu933rnv_uaEwlJ0NhuKbjvwmlEJkU1nkoKcRnexR0_sQemrKdW877Lclh_JXcBkFl1FweRAcL24O5Zuqo_qf_zMqfwDWQnnr</recordid><startdate>20190621</startdate><enddate>20190621</enddate><creator>Hill, Jarvis</creator><creator>Tam, William</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1375-881X</orcidid></search><sort><creationdate>20190621</creationdate><title>Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes</title><author>Hill, Jarvis ; Tam, William</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hill, Jarvis</creatorcontrib><creatorcontrib>Tam, William</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hill, Jarvis</au><au>Tam, William</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2019-06-21</date><risdate>2019</risdate><volume>84</volume><issue>12</issue><spage>8309</spage><epage>8314</epage><pages>8309-8314</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The palladium/Lewis acid cocatalyzed ring-opening reaction of various C -substituted unsymmetrical oxabenzonorbornadienes (OBD) with oxime nucleophiles was investigated. The effects of various C substituents were explored. Moderate to excellent yields and excellent regioselectivities were obtained for electron-withdrawing groups. The presence of electron-donating alkyl groups leads to isomerization of the corresponding OBD to afford the substituted naphthol derivatives. Additionally, a mechanism for the formation of C regioisomeric ring-opened products has been proposed.</abstract><cop>United States</cop><pmid>31192590</pmid><doi>10.1021/acs.joc.9b01094</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-1375-881X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2019-06, Vol.84 (12), p.8309-8314
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2248376098
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Palladium/Lewis Acid Cocatalyzed Ring-Opening Reactions of Unsymmetrical Oxabenzonobornadienes with Oximes
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T18%3A56%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Palladium/Lewis%20Acid%20Cocatalyzed%20Ring-Opening%20Reactions%20of%20Unsymmetrical%20Oxabenzonobornadienes%20with%20Oximes&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Hill,%20Jarvis&rft.date=2019-06-21&rft.volume=84&rft.issue=12&rft.spage=8309&rft.epage=8314&rft.pages=8309-8314&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.9b01094&rft_dat=%3Cproquest_cross%3E2248376098%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c297t-592869e2048a35dcf3beea5437a0d769a7fb2700c70613bd2e19a3a59acadc143%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2248376098&rft_id=info:pmid/31192590&rfr_iscdi=true