{"id":"https://openalex.org/W2008462282","doi":"https://doi.org/10.1021/ja0617688","title":"Experimental Probe for Hyperconjugative Resonance Contribution in Stabilizing the Singlet State of 2,2-Dialkoxy-1,3-diyls: Regioselective 1,2-Oxygen Migration","display_name":"Experimental Probe for Hyperconjugative Resonance Contribution in Stabilizing the Singlet State of 2,2-Dialkoxy-1,3-diyls: Regioselective 1,2-Oxygen Migration","publication_year":2006,"publication_date":"2006-05-24","ids":{"openalex":"https://openalex.org/W2008462282","doi":"https://doi.org/10.1021/ja0617688","mag":"2008462282","pmid":"https://pubmed.ncbi.nlm.nih.gov/16771516"},"language":"en","primary_location":{"id":"doi:10.1021/ja0617688","doi":"https://doi.org/10.1021/ja0617688","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja0617688","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5087548495","display_name":"Manabu Abe","orcid":"https://orcid.org/0000-0002-2013-4394","observed_orcids":["https://orcid.org/0000-0002-2013-4394"]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Manabu Abe","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5083259497","display_name":"Masanori Hattori","orcid":"https://orcid.org/0009-0005-7506-7001","observed_orcids":["https://orcid.org/0009-0005-7506-7001"]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Masanori Hattori","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5057872999","display_name":"Akinobu Takegami","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Akinobu Takegami","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5001011338","display_name":"Araki Masuyama","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Araki Masuyama","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5021407407","display_name":"Takashi Hayashi","orcid":"https://orcid.org/0000-0002-2215-935X","observed_orcids":["https://orcid.org/0000-0002-2215-935X"]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Takashi Hayashi","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5045506489","display_name":"Shu Seki","orcid":"https://orcid.org/0000-0001-7851-4405","observed_orcids":["https://orcid.org/0000-0001-7851-4405"]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Shu Seki","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5074819917","display_name":"Seiichi Tagawa","orcid":"https://orcid.org/0000-0001-7080-0554","observed_orcids":["https://orcid.org/0000-0001-7080-0554"]},"institutions":[{"id":"https://openalex.org/I4405287424","display_name":"The Institute of Scientific and Industrial Research, The University of Osaka","ror":"https://ror.org/053t3hh85","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]},{"id":"https://openalex.org/I98285908","display_name":"The University of Osaka","ror":"https://ror.org/035t8zc32","country_code":"JP","type":"education","lineage":["https://openalex.org/I98285908"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Seiichi Tagawa","raw_affiliation_strings":["Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Contribution from the Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan, and the Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki 565-0047, Osaka, Japan","institution_ids":["https://openalex.org/I4405287424","https://openalex.org/I98285908"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":2.5032,"has_fulltext":false,"cited_by_count":36,"citation_normalized_percentile":{"value":0.88675933,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":87,"max":97},"biblio":{"volume":"128","issue":"24","first_page":"8008","last_page":"8014"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13253","display_name":"Photolysis and Reactive Intermediates","score":0.7318999767303467,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T13253","display_name":"Photolysis and Reactive Intermediates","score":0.7318999767303467,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T11298","display_name":"Synthesis and Properties of Aromatic Compounds","score":0.0778999999165535,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T12893","display_name":"Organic Chemistry Cycloaddition Reactions","score":0.03460000082850456,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/hyperconjugation","display_name":"hyperconjugation","score":0.878000020980835},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.9340000152587891},{"id":"https://openalex.org/keywords/electron-donating-substituents","display_name":"electron-donating substituents","score":0.6150000095367432}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9448593258857727},{"id":"https://openalex.org/C59759590","wikidata":"https://www.wikidata.org/wiki/Q2275927","display_name":"Regioselectivity","level":3,"score":0.9292443990707397},{"id":"https://openalex.org/C177186529","wikidata":"https://www.wikidata.org/wiki/Q899217","display_name":"Hyperconjugation","level":3,"score":0.8358281254768372},{"id":"https://openalex.org/C2777516457","wikidata":"https://www.wikidata.org/wiki/Q2413613","display_name":"Singlet oxygen","level":3,"score":0.7576842308044434},{"id":"https://openalex.org/C33062035","wikidata":"https://www.wikidata.org/wiki/Q3296863","display_name":"Singlet state","level":3,"score":0.6584944725036621},{"id":"https://openalex.org/C139210041","wikidata":"https://www.wikidata.org/wiki/Q2145840","display_name":"Resonance (particle physics)","level":2,"score":0.6010752320289612},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.565872073173523},{"id":"https://openalex.org/C540031477","wikidata":"https://www.wikidata.org/wiki/Q629","display_name":"Oxygen","level":2,"score":0.5545051097869873},{"id":"https://openalex.org/C90150868","wikidata":"https://www.wikidata.org/wiki/Q39513","display_name":"Alkoxy group","level":3,"score":0.5394083261489868},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.36115461587905884},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.2423250377178192},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.13709819316864014},{"id":"https://openalex.org/C181500209","wikidata":"https://www.wikidata.org/wiki/Q215328","display_name":"Excited state","level":2,"score":0.12028402090072632},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.0812770426273346},{"id":"https://openalex.org/C184779094","wikidata":"https://www.wikidata.org/wiki/Q26383","display_name":"Atomic physics","level":1,"score":0.06596532464027405},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.05690181255340576},{"id":"https://openalex.org/C121332964","wikidata":"https://www.wikidata.org/wiki/Q413","display_name":"Physics","level":0,"score":0.0}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1021/ja0617688","doi":"https://doi.org/10.1021/ja0617688","is_oa":false,"landing_page_url":"https://doi.org/10.1021/ja0617688","pdf_url":null,"source":{"id":"https://openalex.org/S111155417","display_name":"Journal of the American Chemical Society","issn_l":"0002-7863","issn":["0002-7863","1520-5126","1943-2984"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-3","ki-jl-3","medline","norway-2","poland-200","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"journal-article"},{"id":"pmid:16771516","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/16771516","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Journal of the American Chemical Society","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":19,"referenced_works":["https://openalex.org/W1975701661","https://openalex.org/W1978942089","https://openalex.org/W1982612764","https://openalex.org/W1989226389","https://openalex.org/W1995777750","https://openalex.org/W2001557358","https://openalex.org/W2006947798","https://openalex.org/W2008844584","https://openalex.org/W2011950471","https://openalex.org/W2085760242","https://openalex.org/W2093623874","https://openalex.org/W2094642658","https://openalex.org/W2097026749","https://openalex.org/W2113844301","https://openalex.org/W2316223553","https://openalex.org/W2334388923","https://openalex.org/W2952547593","https://openalex.org/W3004692941","https://openalex.org/W4250314372"],"related_works":["https://openalex.org/W2088986030","https://openalex.org/W1980955211","https://openalex.org/W2081728297","https://openalex.org/W2131701505","https://openalex.org/W2949166311","https://openalex.org/W2032537557","https://openalex.org/W2316548484","https://openalex.org/W2321214962","https://openalex.org/W1988634668","https://openalex.org/W2107585082"],"abstract_inverted_index":{"A":[0],"detailed":[1],"study":[2],"of":[3,6,31,56],"the":[4,12,24,48,54,60],"regioselectivity":[5],"1,2-oxygen":[7],"migration":[8,30],"was":[9],"conducted":[10],"using":[11],"unsymmetrically":[13],"substituted":[14],"singlet":[15,44,61],"2,2-dialkoxy-1,3-diarylcyclopentane-1,3-diyls":[16],"5.":[17],"The":[18,28],"alkoxy":[19],"group":[20],"selectively":[21],"migrates":[22],"to":[23,51,58],"electron-donating":[25],"p-methoxyphenyl-substituted":[26],"carbon.":[27],"regioselective":[29],"oxygen":[32],"clearly":[33],"indicates":[34],"a":[35],"hyperconjugative":[36],"resonance":[37],"structure,":[38],"that":[39],"is,":[40],"zwitterionic":[41],"characteristics,":[42],"in":[43],"2,2-dialkoxy-1,3-diyls.":[45],"This":[46],"represents":[47],"first":[49],"attempt":[50],"experimentally":[52],"probe":[53],"contribution":[55],"hyperconjugation":[57],"stabilizing":[59],"state.":[62]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2025,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":1},{"year":2019,"cited_by_count":1},{"year":2015,"cited_by_count":4},{"year":2014,"cited_by_count":1},{"year":2013,"cited_by_count":1},{"year":2012,"cited_by_count":3}],"updated_date":"2026-10-24T09:50:30.924529","created_date":"2016-06-24T00:00:00"}
