{"id":"https://openalex.org/W4281632057","doi":"https://doi.org/10.1021/acs.orglett.2c01627","title":"Synthesis of Highly Congested Tertiary Alcohols via the [3,3] Radical Deconstruction of Breslow Intermediates","display_name":"Synthesis of Highly Congested Tertiary Alcohols via the [3,3] Radical Deconstruction of Breslow Intermediates","publication_year":2022,"publication_date":"2022-06-03","ids":{"openalex":"https://openalex.org/W4281632057","doi":"https://doi.org/10.1021/acs.orglett.2c01627","pmid":"https://pubmed.ncbi.nlm.nih.gov/35657720","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/9502203"},"language":"en","primary_location":{"id":"doi:10.1021/acs.orglett.2c01627","doi":"https://doi.org/10.1021/acs.orglett.2c01627","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.2c01627","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/626c8257742e9fb58470a94e/original/synthesis-of-highly-congested-tertiary-alcohols-via-the-3-3-radical-deconstruction-of-breslow-intermediates.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5068945425","display_name":"Roger Mach\u00edn Rivera","orcid":"https://orcid.org/0000-0002-8635-4568","observed_orcids":["https://orcid.org/0000-0002-8635-4568"]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Roger Mach\u00edn Rivera","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5004230721","display_name":"Nikolas R. Burton","orcid":"https://orcid.org/0000-0003-2887-8846","observed_orcids":["https://orcid.org/0000-0003-2887-8846"]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Nikolas R. Burton","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5076976261","display_name":"Luke D. Call","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Luke D. Call","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5022008100","display_name":"Marshall A. Tomat","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Marshall A. Tomat","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States","institution_ids":["https://openalex.org/I137902535"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5000910820","display_name":"Vincent N. G. Lindsay","orcid":"https://orcid.org/0000-0002-7126-325X","observed_orcids":["https://orcid.org/0000-0002-7126-325X"]},"institutions":[{"id":"https://openalex.org/I137902535","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06","country_code":"US","type":"education","lineage":["https://openalex.org/I137902535"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Vincent N. G. Lindsay","raw_affiliation_strings":["Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States"],"raw_orcid":"https://orcid.org/0000-0002-7126-325X","affiliations":[{"raw_affiliation_string":"Department of Chemistry, North Carolina State University, 2620 Yarbrough Drive, Raleigh, North Carolina 27695, United States","institution_ids":["https://openalex.org/I137902535"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":["https://openalex.org/A5000910820"],"corresponding_institution_ids":["https://openalex.org/I137902535"],"apc_list":{"value":5000,"currency":"USD","value_usd":5000},"apc_paid":null,"fwci":0.3752,"has_fulltext":false,"cited_by_count":4,"citation_normalized_percentile":{"value":0.41040673,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":95},"biblio":{"volume":"24","issue":"23","first_page":"4275","last_page":"4280"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10701","display_name":"Radical Photochemical Reactions","score":0.4790000021457672,"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/T10701","display_name":"Radical Photochemical Reactions","score":0.4790000021457672,"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/T11790","display_name":"N-Heterocyclic Carbenes in Organic and Inorganic Chemistry","score":0.29490000009536743,"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/T11611","display_name":"Cyclopropane Reaction Mechanisms","score":0.0771000012755394,"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/tertiary-alcohols","display_name":"tertiary alcohols","score":0.8939999938011169},{"id":"https://openalex.org/keywords/3-3-sigmatropic-rearrangement","display_name":"[3,3]-sigmatropic rearrangement","score":0.878000020980835},{"id":"https://openalex.org/keywords/breslow-intermediate","display_name":"Breslow intermediate","score":0.9679999947547913},{"id":"https://openalex.org/keywords/substituted-benzaldehydes","display_name":"benzaldehyde derivatives","score":0.9340000152587891},{"id":"https://openalex.org/keywords/radical-pairs","display_name":"radical pairs","score":0.546999990940094},{"id":"https://openalex.org/keywords/radical-recombination","display_name":"radical recombination","score":0.6449999809265137},{"id":"https://openalex.org/keywords/regioselectivity","display_name":"regioselectivity","score":0.906000018119812},{"id":"https://openalex.org/keywords/diastereoselectivity","display_name":"diastereoselectivity","score":0.996999979019165},{"id":"https://openalex.org/keywords/hindered-alcohols","display_name":"hindered alcohols","score":0.8410000205039978}],"concepts":[{"id":"https://openalex.org/C171999351","wikidata":"https://www.wikidata.org/wiki/Q898403","display_name":"Pericyclic reaction","level":2,"score":0.9213275909423828},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8969149589538574},{"id":"https://openalex.org/C58590140","wikidata":"https://www.wikidata.org/wiki/Q306614","display_name":"Sigmatropic reaction","level":2,"score":0.7440245747566223},{"id":"https://openalex.org/C2779692420","wikidata":"https://www.wikidata.org/wiki/Q372524","display_name":"Benzaldehyde","level":3,"score":0.6171307563781738},{"id":"https://openalex.org/C2776254738","wikidata":"https://www.wikidata.org/wiki/Q81406","display_name":"Alkene","level":3,"score":0.4778806269168854},{"id":"https://openalex.org/C96350342","wikidata":"https://www.wikidata.org/wiki/Q905087","display_name":"Cope rearrangement","level":2,"score":0.4727500379085541},{"id":"https://openalex.org/C2909312076","wikidata":"https://www.wikidata.org/wiki/Q156","display_name":"Tertiary alcohols","level":3,"score":0.41258862614631653},{"id":"https://openalex.org/C105768512","wikidata":"https://www.wikidata.org/wiki/Q7458208","display_name":"Reaction intermediate","level":3,"score":0.4122731685638428},{"id":"https://openalex.org/C2781066024","wikidata":"https://www.wikidata.org/wiki/Q156","display_name":"Alcohol","level":2,"score":0.3396757245063782},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3369799852371216},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.1322222352027893}],"mesh":[{"descriptor_ui":"D000438","descriptor_name":"Alcohols","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true}],"locations_count":4,"locations":[{"id":"doi:10.1021/acs.orglett.2c01627","doi":"https://doi.org/10.1021/acs.orglett.2c01627","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.2c01627","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"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":"Organic Letters","raw_type":"journal-article"},{"id":"doi:10.26434/chemrxiv-2022-l60sc","doi":"https://doi.org/10.26434/chemrxiv-2022-l60sc","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv-2022-l60sc","pdf_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/626c8257742e9fb58470a94e/original/synthesis-of-highly-congested-tertiary-alcohols-via-the-3-3-radical-deconstruction-of-breslow-intermediates.pdf","source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},{"id":"pmid:35657720","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/35657720","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":"Organic letters","raw_type":"Journal Article"},{"id":"pmh:oai:pubmedcentral.nih.gov:9502203","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/9502203","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":"Org Lett","raw_type":"Text"}],"best_oa_location":{"id":"doi:10.26434/chemrxiv-2022-l60sc","doi":"https://doi.org/10.26434/chemrxiv-2022-l60sc","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv-2022-l60sc","pdf_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/626c8257742e9fb58470a94e/original/synthesis-of-highly-congested-tertiary-alcohols-via-the-3-3-radical-deconstruction-of-breslow-intermediates.pdf","source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G9000889391","display_name":"Unlocking Access to Cyclopropanones as Divergent Reactive Intermediates in Synthesis","funder_award_id":"R35GM142965","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"}],"funders":[{"id":"https://openalex.org/F4320310013","display_name":"North Carolina State University","ror":"https://ror.org/04tj63d06"},{"id":"https://openalex.org/F4320332161","display_name":"National Institutes of Health","ror":"https://ror.org/01cwqze88"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4281632057.pdf","grobid_xml":"https://content.openalex.org/works/W4281632057.grobid-xml"},"referenced_works_count":91,"referenced_works":["https://openalex.org/W1163011906","https://openalex.org/W1504113608","https://openalex.org/W1583170487","https://openalex.org/W1837410261","https://openalex.org/W1916349588","https://openalex.org/W1944138010","https://openalex.org/W1966510752","https://openalex.org/W1966983316","https://openalex.org/W1968887784","https://openalex.org/W1971250545","https://openalex.org/W1981670174","https://openalex.org/W1984739513","https://openalex.org/W1987083186","https://openalex.org/W1991983378","https://openalex.org/W1997139700","https://openalex.org/W2003555872","https://openalex.org/W2016450375","https://openalex.org/W2018729897","https://openalex.org/W2032263820","https://openalex.org/W2033512764","https://openalex.org/W2038092103","https://openalex.org/W2038140869","https://openalex.org/W2043304555","https://openalex.org/W2048122722","https://openalex.org/W2062311935","https://openalex.org/W2072591300","https://openalex.org/W2074274985","https://openalex.org/W2078309396","https://openalex.org/W2081054292","https://openalex.org/W2083357654","https://openalex.org/W2089129060","https://openalex.org/W2099873677","https://openalex.org/W2101157774","https://openalex.org/W2121360698","https://openalex.org/W2126662293","https://openalex.org/W2132802917","https://openalex.org/W2157799374","https://openalex.org/W2159094116","https://openalex.org/W2162846787","https://openalex.org/W2299637886","https://openalex.org/W2314431251","https://openalex.org/W2318894119","https://openalex.org/W2320163706","https://openalex.org/W2320679824","https://openalex.org/W2320791033","https://openalex.org/W2326865649","https://openalex.org/W2329172050","https://openalex.org/W2413961131","https://openalex.org/W2418293022","https://openalex.org/W2520733385","https://openalex.org/W2551229502","https://openalex.org/W2553736986","https://openalex.org/W2592126099","https://openalex.org/W2608095815","https://openalex.org/W2739196637","https://openalex.org/W2756128373","https://openalex.org/W2783272569","https://openalex.org/W2785313861","https://openalex.org/W2796895606","https://openalex.org/W2903777026","https://openalex.org/W2908564514","https://openalex.org/W2915743380","https://openalex.org/W2920806128","https://openalex.org/W2947141118","https://openalex.org/W2952399985","https://openalex.org/W2970991365","https://openalex.org/W2972586158","https://openalex.org/W2993702856","https://openalex.org/W2997313217","https://openalex.org/W3013073252","https://openalex.org/W3017712261","https://openalex.org/W3020976311","https://openalex.org/W3023376281","https://openalex.org/W3034092520","https://openalex.org/W3035784503","https://openalex.org/W3044817820","https://openalex.org/W3083604264","https://openalex.org/W3092301630","https://openalex.org/W3124681459","https://openalex.org/W3128941850","https://openalex.org/W3160966795","https://openalex.org/W3162211292","https://openalex.org/W3164785601","https://openalex.org/W3175760115","https://openalex.org/W3197633608","https://openalex.org/W3206787077","https://openalex.org/W3207871969","https://openalex.org/W4210984382","https://openalex.org/W4235250507","https://openalex.org/W4244843427","https://openalex.org/W6701377599"],"related_works":["https://openalex.org/W1971250545","https://openalex.org/W2951836324","https://openalex.org/W3213645962","https://openalex.org/W2951275142","https://openalex.org/W7030453622","https://openalex.org/W4402093282","https://openalex.org/W2322822694","https://openalex.org/W2092327836","https://openalex.org/W4311540089","https://openalex.org/W2141891962"],"abstract_inverted_index":{"Pericyclic":[0],"processes":[1],"such":[2],"as":[3],"[3,3]-sigmatropic":[4],"rearrangements":[5],"leading":[6,71],"to":[7,72],"the":[8,24,54],"rapid":[9],"generation":[10],"of":[11,26,33],"molecular":[12],"complexity":[13],"constitute":[14],"highly":[15],"valuable":[16],"tools":[17],"in":[18,37,64],"organic":[19],"synthesis.":[20],"Herein,":[21],"we":[22],"report":[23],"formation":[25],"particularly":[27],"hindered":[28],"tertiary":[29],"alcohols":[30],"via":[31,57],"rearrangement":[32],"Breslow":[34],"intermediates":[35],"formed":[36],"situ":[38],"from":[39],"readily":[40],"available":[41],"N-allyl":[42],"thiazolium":[43],"salts":[44],"and":[45,67],"benzaldehyde":[46],"derivatives.":[47],"Experimental":[48],"mechanistic":[49],"studies":[50],"performed":[51],"suggest":[52],"that":[53],"reaction":[55],"proceeds":[56],"a":[58,65],"close":[59],"radical":[60],"pair":[61],"which":[62],"recombine":[63],"regio-":[66],"diastereoselective":[68],"manner,":[69],"formally":[70],"[3,3]-rearranged":[73],"products.":[74]},"counts_by_year":[{"year":2024,"cited_by_count":2},{"year":2023,"cited_by_count":1},{"year":2022,"cited_by_count":1}],"updated_date":"2026-11-03T10:50:19.383937","created_date":"2022-06-13T00:00:00"}
