{"id":"https://openalex.org/W2884097537","doi":"https://doi.org/10.1021/acs.joc.8b01590","title":"Synthesis of Halogenated Anilines by Treatment of N,N-Dialkylaniline N-Oxides with Thionyl Halides","display_name":"Synthesis of Halogenated Anilines by Treatment of N,N-Dialkylaniline N-Oxides with Thionyl Halides","publication_year":2018,"publication_date":"2018-07-26","ids":{"openalex":"https://openalex.org/W2884097537","doi":"https://doi.org/10.1021/acs.joc.8b01590","mag":"2884097537","pmid":"https://pubmed.ncbi.nlm.nih.gov/30048135","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/6745195"},"language":"en","primary_location":{"id":"doi:10.1021/acs.joc.8b01590","doi":"https://doi.org/10.1021/acs.joc.8b01590","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.8b01590","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":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6745195","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":null,"display_name":"Hayley Reed","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I86501945","display_name":"University of Delaware","ror":"https://ror.org/01sbq1a82","country_code":"US","type":"education","lineage":["https://openalex.org/I86501945"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Hayley Reed","raw_affiliation_strings":["Department of Chemistry & Biochemistry University of Delaware Newark, Delaware 19716, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry University of Delaware Newark, Delaware 19716, United States","institution_ids":["https://openalex.org/I86501945"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5084715875","display_name":"Tyler R. Paul","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I86501945","display_name":"University of Delaware","ror":"https://ror.org/01sbq1a82","country_code":"US","type":"education","lineage":["https://openalex.org/I86501945"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Tyler R. Paul","raw_affiliation_strings":["Department of Chemistry & Biochemistry University of Delaware Newark, Delaware 19716, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry University of Delaware Newark, Delaware 19716, United States","institution_ids":["https://openalex.org/I86501945"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5034753312","display_name":"William J. Chain","orcid":"https://orcid.org/0000-0003-0312-6250","observed_orcids":["https://orcid.org/0000-0003-0312-6250"]},"institutions":[{"id":"https://openalex.org/I86501945","display_name":"University of Delaware","ror":"https://ror.org/01sbq1a82","country_code":"US","type":"education","lineage":["https://openalex.org/I86501945"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"William J. Chain","raw_affiliation_strings":["Department of Chemistry & Biochemistry University of Delaware Newark, Delaware 19716, United States"],"raw_orcid":"https://orcid.org/0000-0003-0312-6250","affiliations":[{"raw_affiliation_string":"Department of Chemistry & Biochemistry University of Delaware Newark, Delaware 19716, United States","institution_ids":["https://openalex.org/I86501945"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5034753312"],"corresponding_institution_ids":["https://openalex.org/I86501945"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":0.4093,"has_fulltext":false,"cited_by_count":13,"citation_normalized_percentile":{"value":0.4804685,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":97},"biblio":{"volume":"83","issue":"18","first_page":"11359","last_page":"11368"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11831","display_name":"Chemical Synthesis and Reactions","score":0.17440000176429749,"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"}},"topics":[{"id":"https://openalex.org/T11831","display_name":"Chemical Synthesis and Reactions","score":0.17440000176429749,"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/T10701","display_name":"Radical Photochemical Reactions","score":0.13109999895095825,"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/T12189","display_name":"Sulfur-Based Synthesis Techniques","score":0.1306000053882599,"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/halogenated-anilines","display_name":"halogenated anilines","score":0.9829999804496765},{"id":"https://openalex.org/keywords/thionyl-bromide","display_name":"thionyl bromide","score":0.9779999852180481},{"id":"https://openalex.org/keywords/thionyl-chloride","display_name":"thionyl chloride","score":1.0},{"id":"https://openalex.org/keywords/aryl-halides","display_name":"aryl halides","score":0.7080000042915344},{"id":"https://openalex.org/keywords/n-o-bond-cleavage","display_name":"N-O bond cleavage","score":0.722000002861023},{"id":"https://openalex.org/keywords/regioselective-halogenation","display_name":"regioselective halogenation","score":0.6600000262260437}],"concepts":[{"id":"https://openalex.org/C2776942435","wikidata":"https://www.wikidata.org/wiki/Q409171","display_name":"Thionyl chloride","level":3,"score":0.9715029001235962},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9501457810401917},{"id":"https://openalex.org/C171560689","wikidata":"https://www.wikidata.org/wiki/Q193086","display_name":"Halide","level":2,"score":0.8418547511100769},{"id":"https://openalex.org/C65973085","wikidata":"https://www.wikidata.org/wiki/Q888529","display_name":"Halogenation","level":2,"score":0.7426450252532959},{"id":"https://openalex.org/C134121241","wikidata":"https://www.wikidata.org/wiki/Q899301","display_name":"Yield (engineering)","level":2,"score":0.6505099534988403},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.6286808252334595},{"id":"https://openalex.org/C2776300020","wikidata":"https://www.wikidata.org/wiki/Q422423","display_name":"Bromide","level":2,"score":0.6055400371551514},{"id":"https://openalex.org/C2776910235","wikidata":"https://www.wikidata.org/wiki/Q18574","display_name":"Reactivity (psychology)","level":3,"score":0.5693551301956177},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.5228881239891052},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.41724666953086853},{"id":"https://openalex.org/C2778695967","wikidata":"https://www.wikidata.org/wiki/Q44791900","display_name":"Chloride","level":2,"score":0.3984149098396301},{"id":"https://openalex.org/C179104552","wikidata":"https://www.wikidata.org/wiki/Q11165","display_name":"Inorganic chemistry","level":1,"score":0.3268815875053406},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.14615243673324585},{"id":"https://openalex.org/C192562407","wikidata":"https://www.wikidata.org/wiki/Q228736","display_name":"Materials science","level":0,"score":0.0},{"id":"https://openalex.org/C204787440","wikidata":"https://www.wikidata.org/wiki/Q188504","display_name":"Alternative medicine","level":2,"score":0.0},{"id":"https://openalex.org/C142724271","wikidata":"https://www.wikidata.org/wiki/Q7208","display_name":"Pathology","level":1,"score":0.0},{"id":"https://openalex.org/C71924100","wikidata":"https://www.wikidata.org/wiki/Q11190","display_name":"Medicine","level":0,"score":0.0},{"id":"https://openalex.org/C191897082","wikidata":"https://www.wikidata.org/wiki/Q11467","display_name":"Metallurgy","level":1,"score":0.0}],"mesh":[{"descriptor_ui":"D000814","descriptor_name":"Aniline Compounds","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D000814","descriptor_name":"Aniline Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D010087","descriptor_name":"Oxides","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D054879","descriptor_name":"Halogenation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D060326","descriptor_name":"Chemistry Techniques, Synthetic","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.joc.8b01590","doi":"https://doi.org/10.1021/acs.joc.8b01590","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.joc.8b01590","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:30048135","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/30048135","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"},{"id":"pmh:oai:pubmedcentral.nih.gov:6745195","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6745195","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"J Org Chem","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:6745195","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/6745195","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"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":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"J Org Chem","raw_type":"Text"},"sustainable_development_goals":[],"sustainable_development_goals_aurora":[{"display_name":"Clean water and sanitation","id":"https://metadata.un.org/sdg/6","score":0.7699999809265137}],"study_designs":[],"awards":[{"id":"https://openalex.org/G1617517245","display_name":null,"funder_award_id":"54452-ND1","funder_id":"https://openalex.org/F4320332454","funder_display_name":"American Chemical Society Petroleum Research Fund"},{"id":"https://openalex.org/G2144188405","display_name":null,"funder_award_id":"CHE1664954","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G3037964080","display_name":"Discovery of Chemical Probes and Therapeutic Leads, Phase II","funder_award_id":"P20GM104316","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G335888736","display_name":null,"funder_award_id":"CHE 0840401","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G4040836280","display_name":null,"funder_award_id":"CHE1048367","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G501384772","display_name":null,"funder_award_id":"CHE 0421224","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G5679962385","display_name":null,"funder_award_id":"CHE 1229234","funder_id":"https://openalex.org/F4320337393","funder_display_name":"Division of Chemistry"},{"id":"https://openalex.org/G6204561026","display_name":null,"funder_award_id":"S10 OD016267-01","funder_id":"https://openalex.org/F4320337349","funder_display_name":"NIH Office of the Director"},{"id":"https://openalex.org/G7558382895","display_name":"High Performance Digital NMR Spectrometer","funder_award_id":"S10RR026962","funder_id":"https://openalex.org/F4320337375","funder_display_name":"National Center for Research Resources"},{"id":"https://openalex.org/G8612150275","display_name":"Molecular Design of Advanced Biomaterials","funder_award_id":"P30GM110758","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G93081233","display_name":"Q-Exactive Orbitrap LC-MC/MS System","funder_award_id":"1s10od016267-01","funder_id":"https://openalex.org/F4320332161","funder_display_name":"National Institutes of Health"}],"funders":[{"id":"https://openalex.org/F4320308928","display_name":"University of Delaware","ror":"https://ror.org/01sbq1a82"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320332454","display_name":"American Chemical Society Petroleum Research Fund","ror":"https://ror.org/059dqb057"},{"id":"https://openalex.org/F4320337349","display_name":"NIH Office of the Director","ror":"https://ror.org/00fj8a872"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"},{"id":"https://openalex.org/F4320337375","display_name":"National Center for Research Resources","ror":"https://ror.org/04pw6fb54"},{"id":"https://openalex.org/F4320337393","display_name":"Division of Chemistry","ror":"https://ror.org/01ar8dr59"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":38,"referenced_works":["https://openalex.org/W46105479","https://openalex.org/W280137907","https://openalex.org/W340172793","https://openalex.org/W565854973","https://openalex.org/W1964297120","https://openalex.org/W1971958979","https://openalex.org/W1973284237","https://openalex.org/W1976526015","https://openalex.org/W1982346259","https://openalex.org/W1994863403","https://openalex.org/W1997630328","https://openalex.org/W2000466466","https://openalex.org/W2006003563","https://openalex.org/W2011776726","https://openalex.org/W2013760130","https://openalex.org/W2019249602","https://openalex.org/W2026855686","https://openalex.org/W2031045380","https://openalex.org/W2041354986","https://openalex.org/W2066065078","https://openalex.org/W2069607377","https://openalex.org/W2078574568","https://openalex.org/W2086309432","https://openalex.org/W2130371225","https://openalex.org/W2321894438","https://openalex.org/W2323973790","https://openalex.org/W2331587229","https://openalex.org/W2413113094","https://openalex.org/W2489743576","https://openalex.org/W2504171849","https://openalex.org/W2736941216","https://openalex.org/W2949206821","https://openalex.org/W2949744654","https://openalex.org/W2996105227","https://openalex.org/W3023376281","https://openalex.org/W4232945307","https://openalex.org/W4235593749","https://openalex.org/W4301085298"],"related_works":["https://openalex.org/W2413113094","https://openalex.org/W2087357712","https://openalex.org/W2072849311","https://openalex.org/W4409645924","https://openalex.org/W3155442483","https://openalex.org/W2802917775","https://openalex.org/W2026855686","https://openalex.org/W2950273911","https://openalex.org/W1598391496","https://openalex.org/W3159227522"],"abstract_inverted_index":{"The":[0,36],"special":[1],"reactivity":[2],"of":[3,18,28,38,42,54,64],"N,N-dialkylaniline":[4,59],"N-oxides":[5,60],"allows":[6],"practical":[7],"and":[8,61],"convenient":[9],"access":[10],"to":[11,32,56],"electron-rich":[12],"aryl":[13],"halides.":[14],"A":[15],"complementary":[16],"pair":[17],"reaction":[19],"protocols":[20],"allow":[21],"for":[22],"the":[23,57,62,65],"selective":[24],"para-bromination":[25],"or":[26,76],"ortho-chlorination":[27],"N,N-dialkylanilines":[29,55],"in":[30],"up":[31],"69%":[33],"isolated":[34],"yield.":[35],"generation":[37],"a":[39,49],"diverse":[40],"array":[41],"halogenated":[43],"anilines":[44],"is":[45],"made":[46],"possible":[47],"by":[48],"temporary":[50],"oxidation":[51],"level":[52],"increase":[53],"corresponding":[58],"excision":[63],"resultant":[66],"weak":[67],"N-":[68],"O":[69],"bond":[70],"via":[71],"treatment":[72],"with":[73],"thionyl":[74,77],"bromide":[75],"chloride":[78],"at":[79],"low":[80],"temperature.":[81]},"counts_by_year":[{"year":2026,"cited_by_count":1},{"year":2025,"cited_by_count":2},{"year":2024,"cited_by_count":1},{"year":2023,"cited_by_count":4},{"year":2022,"cited_by_count":1},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":1}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2018-08-03T00:00:00"}