{"id":"https://openalex.org/W2686057698","doi":"https://doi.org/10.1021/acs.joc.7b00927","title":"Photochemical Cleavage of Benzylic C\u2013O Bond Facilitated by an Ortho or Meta Amino Group","display_name":"Photochemical Cleavage of Benzylic C\u2013O Bond Facilitated by an Ortho or Meta Amino Group","publication_year":2017,"publication_date":"2017-06-23","ids":{"openalex":"https://openalex.org/W2686057698","doi":"https://doi.org/10.1021/acs.joc.7b00927","mag":"2686057698","pmid":"https://pubmed.ncbi.nlm.nih.gov/28643513"},"language":"en","primary_location":{"id":"doi:10.1021/acs.joc.7b00927","doi":"https://doi.org/10.1021/acs.joc.7b00927","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.7b00927","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","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/A5054788092","display_name":"Xiong Ding","orcid":"https://orcid.org/0000-0003-0437-0589","observed_orcids":["https://orcid.org/0000-0003-0437-0589"]},"institutions":[{"id":"https://openalex.org/I32389192","display_name":"University of Alabama at Birmingham","ror":"https://ror.org/008s83205","country_code":"US","type":"education","lineage":["https://openalex.org/I32389192"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Xiong Ding","raw_affiliation_strings":["Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, Alabama 35294, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, Alabama 35294, United States","institution_ids":["https://openalex.org/I32389192"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5100399545","display_name":"Pengfei Wang","orcid":"https://orcid.org/0000-0002-0285-2069","observed_orcids":["https://orcid.org/0000-0002-0285-2069"]},"institutions":[{"id":"https://openalex.org/I32389192","display_name":"University of Alabama at Birmingham","ror":"https://ror.org/008s83205","country_code":"US","type":"education","lineage":["https://openalex.org/I32389192"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Pengfei Wang","raw_affiliation_strings":["Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, Alabama 35294, United States"],"raw_orcid":"https://orcid.org/0000-0002-0285-2069","affiliations":[{"raw_affiliation_string":"Department of Chemistry, University of Alabama at Birmingham, 901 14th Street South, Birmingham, Alabama 35294, United States","institution_ids":["https://openalex.org/I32389192"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5100399545"],"corresponding_institution_ids":["https://openalex.org/I32389192"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.1549,"has_fulltext":false,"cited_by_count":19,"citation_normalized_percentile":{"value":0.751125,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"82","issue":"14","first_page":"7309","last_page":"7316"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11708","display_name":"Photochromic and Fluorescence Chemistry","score":0.8690999746322632,"subfield":{"id":"https://openalex.org/subfields/2505","display_name":"Materials Chemistry"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T11708","display_name":"Photochromic and Fluorescence Chemistry","score":0.8690999746322632,"subfield":{"id":"https://openalex.org/subfields/2505","display_name":"Materials Chemistry"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13253","display_name":"Chemical Reactions and Mechanisms","score":0.07169999927282333,"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/T10701","display_name":"Radical Photochemical Reactions","score":0.02669999934732914,"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/photochemical-cleavage","display_name":"photochemical cleavage","score":0.7269999980926514},{"id":"https://openalex.org/keywords/photolabile-protecting-groups","display_name":"photolabile protecting groups","score":0.8220000267028809},{"id":"https://openalex.org/keywords/amine-release","display_name":"amine release","score":0.5960000157356262}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9455438852310181},{"id":"https://openalex.org/C3044715","wikidata":"https://www.wikidata.org/wiki/Q3952437","display_name":"Bond cleavage","level":3,"score":0.5898328423500061},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.552807092666626},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.5504471063613892},{"id":"https://openalex.org/C2781066024","wikidata":"https://www.wikidata.org/wiki/Q156","display_name":"Alcohol","level":2,"score":0.5274137258529663},{"id":"https://openalex.org/C175156509","wikidata":"https://www.wikidata.org/wiki/Q1990218","display_name":"Cleavage (geology)","level":3,"score":0.5018601417541504},{"id":"https://openalex.org/C2779074116","wikidata":"https://www.wikidata.org/wiki/Q134856","display_name":"Carboxylic acid","level":2,"score":0.4940226674079895},{"id":"https://openalex.org/C33062035","wikidata":"https://www.wikidata.org/wiki/Q3296863","display_name":"Singlet state","level":3,"score":0.48487362265586853},{"id":"https://openalex.org/C181500209","wikidata":"https://www.wikidata.org/wiki/Q215328","display_name":"Excited state","level":2,"score":0.48140954971313477},{"id":"https://openalex.org/C515207424","wikidata":"https://www.wikidata.org/wiki/Q8066","display_name":"Amino acid","level":2,"score":0.44081008434295654},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.38731053471565247},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3504791259765625},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2448197603225708},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.08054912090301514},{"id":"https://openalex.org/C127413603","wikidata":"https://www.wikidata.org/wiki/Q11023","display_name":"Engineering","level":0,"score":0.0},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.0},{"id":"https://openalex.org/C43369102","wikidata":"https://www.wikidata.org/wiki/Q2307625","display_name":"Fracture (geology)","level":2,"score":0.0},{"id":"https://openalex.org/C185544564","wikidata":"https://www.wikidata.org/wiki/Q81197","display_name":"Nuclear physics","level":1,"score":0.0},{"id":"https://openalex.org/C187320778","wikidata":"https://www.wikidata.org/wiki/Q1349130","display_name":"Geotechnical engineering","level":1,"score":0.0},{"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/acs.joc.7b00927","doi":"https://doi.org/10.1021/acs.joc.7b00927","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.7b00927","pdf_url":null,"source":{"id":"https://openalex.org/S205050996","display_name":"The Journal of Organic Chemistry","issn_l":"0022-3263","issn":["0022-3263","1520-6904"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","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":"The Journal of Organic Chemistry","raw_type":"journal-article"},{"id":"pmid:28643513","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/28643513","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":"The Journal of organic chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G1448534312","display_name":null,"funder_award_id":"CHE-1404063","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"}],"funders":[{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":26,"referenced_works":["https://openalex.org/W327769071","https://openalex.org/W954716658","https://openalex.org/W1567134662","https://openalex.org/W1974166800","https://openalex.org/W1988056072","https://openalex.org/W1993960494","https://openalex.org/W1996904453","https://openalex.org/W2017879974","https://openalex.org/W2025395772","https://openalex.org/W2041243006","https://openalex.org/W2047077359","https://openalex.org/W2064595585","https://openalex.org/W2083282573","https://openalex.org/W2125160663","https://openalex.org/W2136698583","https://openalex.org/W2319451853","https://openalex.org/W2320098159","https://openalex.org/W2320483273","https://openalex.org/W2324671529","https://openalex.org/W2325439480","https://openalex.org/W2326596280","https://openalex.org/W2396507334","https://openalex.org/W2528692187","https://openalex.org/W2560062556","https://openalex.org/W2952740360","https://openalex.org/W2976668728"],"related_works":["https://openalex.org/W7154683132","https://openalex.org/W2040993782","https://openalex.org/W2888648108","https://openalex.org/W2720444675","https://openalex.org/W2523225805","https://openalex.org/W2949914676","https://openalex.org/W2396507334","https://openalex.org/W3144279635","https://openalex.org/W1990787288","https://openalex.org/W2560062556"],"abstract_inverted_index":{"The":[0],"excited":[1,33],"state":[2],"meta":[3,22,64,113],"effect,":[4,10],"also":[5,94],"known":[6],"as":[7,66,78],"the":[8,21,49,63,112],"meta-ortho":[9],"results":[11,115],"from":[12,16],"selective":[13],"electron":[14],"transmission":[15],"an":[17,27,57,79,89,102,108],"electron-donating":[18,58],"group":[19,60,77,83,92,110],"to":[20,47,100],"and":[23,123],"ortho":[24,90],"sites":[25],"on":[26],"aromatic":[28],"ring":[29],"in":[30,68,116],"its":[31],"first":[32],"singlet":[34],"state.":[35],"This":[36],"effect":[37],"facilitates":[38],"photochemical":[39,124],"cleavage":[40,99],"of":[41,72],"benzylic":[42,96],"C-O":[43,97],"or":[44,54,104],"C-N":[45],"bond":[46,98],"release":[48,101],"corresponding":[50],"alcohol,":[51],"carboxylic":[52,105],"acid,":[53],"amine":[55],"when":[56],"amino":[59,91,109],"is":[61],"at":[62,111],"position,":[65],"demonstrated":[67],"our":[69],"recent":[70],"work":[71],"using":[73],"a":[74,117],"3-diethylaminobenzyl":[75],"(DEABn)":[76],"effective":[80],"photolabile":[81],"protecting":[82],"(PPG).":[84],"Herein,":[85],"we":[86],"demonstrate":[87],"that":[88],"can":[93],"facilitate":[95],"alcohol":[103],"acid.":[106],"However,":[107],"position":[114],"PPG":[118],"with":[119],"better":[120],"overall":[121],"chemical":[122],"properties.":[125]},"counts_by_year":[{"year":2026,"cited_by_count":2},{"year":2024,"cited_by_count":3},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":2},{"year":2021,"cited_by_count":1},{"year":2019,"cited_by_count":5},{"year":2018,"cited_by_count":3},{"year":2017,"cited_by_count":2}],"updated_date":"2026-10-16T09:59:22.235173","created_date":"2017-06-30T00:00:00"}