{"id":"https://openalex.org/W2073680201","doi":"https://doi.org/10.1139/v81-455","title":"A thermal [1,3] sigmatropic rearrangement: thermolysis of 2,2-bis(ethylthio)-3,3-dimethyl-4-pentenal","display_name":"A thermal [1,3] sigmatropic rearrangement: thermolysis of 2,2-bis(ethylthio)-3,3-dimethyl-4-pentenal","publication_year":1981,"publication_date":"1981-11-01","ids":{"openalex":"https://openalex.org/W2073680201","doi":"https://doi.org/10.1139/v81-455","mag":"2073680201"},"language":"en","primary_location":{"id":"doi:10.1139/v81-455","doi":"https://doi.org/10.1139/v81-455","is_oa":true,"landing_page_url":"https://doi.org/10.1139/v81-455","pdf_url":"https://cdnsciencepub.com/doi/pdf/10.1139/v81-455","source":{"id":"https://openalex.org/S9189650","display_name":"Canadian Journal of Chemistry","issn_l":"0008-4042","issn":["0008-4042","1480-3291"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","norway-1","poland-40","russia-white-list-3"],"host_organization":"https://openalex.org/P4310312929","host_organization_name":"Canadian Science Publishing","host_organization_lineage":["https://openalex.org/P4310312929"],"host_organization_lineage_names":["Canadian Science Publishing"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Canadian Journal of Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":true,"oa_status":"bronze","oa_url":"https://cdnsciencepub.com/doi/pdf/10.1139/v81-455","any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5114004938","display_name":"Gordon S. Bates","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I141945490","display_name":"University of British Columbia","ror":"https://ror.org/03rmrcq20","country_code":"CA","type":"education","lineage":["https://openalex.org/I141945490"]},{"id":"https://openalex.org/I4210159778","display_name":"National Research Council Canada","ror":"https://ror.org/04mte1k06","country_code":"CA","type":"government","lineage":["https://openalex.org/I4210159778"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"Gordon S. Bates","raw_affiliation_strings":["Departtnerzt of Chemistry , Uni~ersity of British Colutnbia , Vancou~er , B.C. , Curlada V6T 11'","Departtnerzt of Chemistry, Uni~ersity of British Colutnbia, Vancou~er, B","National Research Council of Canada/Conseil national de recherches du Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departtnerzt of Chemistry , Uni~ersity of British Colutnbia , Vancou~er , B.C. , Curlada V6T 11'","institution_ids":["https://openalex.org/I141945490"]},{"raw_affiliation_string":"Departtnerzt of Chemistry, Uni~ersity of British Colutnbia, Vancou~er, B","institution_ids":["https://openalex.org/I141945490"]},{"raw_affiliation_string":"National Research Council of Canada/Conseil national de recherches du Canada","institution_ids":["https://openalex.org/I4210159778"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5015165737","display_name":"S. Ramaswamy","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I141945490","display_name":"University of British Columbia","ror":"https://ror.org/03rmrcq20","country_code":"CA","type":"education","lineage":["https://openalex.org/I141945490"]},{"id":"https://openalex.org/I4210159778","display_name":"National Research Council Canada","ror":"https://ror.org/04mte1k06","country_code":"CA","type":"government","lineage":["https://openalex.org/I4210159778"]}],"countries":["CA"],"is_corresponding":false,"raw_author_name":"S. Ramaswamy","raw_affiliation_strings":["Departtnerzt of Chemistry , Uni~ersity of British Colutnbia , Vancou~er , B.C. , Curlada V6T 11'","Departtnerzt of Chemistry, Uni~ersity of British Colutnbia, Vancou~er, B","National Research Council of Canada/Conseil national de recherches du Canada"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departtnerzt of Chemistry , Uni~ersity of British Colutnbia , Vancou~er , B.C. , Curlada V6T 11'","institution_ids":["https://openalex.org/I141945490"]},{"raw_affiliation_string":"Departtnerzt of Chemistry, Uni~ersity of British Colutnbia, Vancou~er, B","institution_ids":["https://openalex.org/I141945490"]},{"raw_affiliation_string":"National Research Council of Canada/Conseil national de recherches du Canada","institution_ids":["https://openalex.org/I4210159778"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":0.3584,"has_fulltext":true,"cited_by_count":6,"citation_normalized_percentile":{"value":0.53529412,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":93,"max":95},"biblio":{"volume":"59","issue":"21","first_page":"3120","last_page":"3122"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T13253","display_name":"Photolysis and Reactive Intermediates","score":0.4790000021457672,"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":0.4790000021457672,"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/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.1860000044107437,"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":0.13130000233650208,"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/1-3-sigmatropic-rearrangement","display_name":"1,3-sigmatropic rearrangement","score":0.949999988079071},{"id":"https://openalex.org/keywords/thermal-isomerization","display_name":"thermal isomerization","score":0.8059999942779541},{"id":"https://openalex.org/keywords/entropy-of-activation","display_name":"activation entropy","score":0.8100000023841858},{"id":"https://openalex.org/keywords/solvent-effects","display_name":"solvent effects","score":0.6650000214576721},{"id":"https://openalex.org/keywords/first-order-kinetics","display_name":"first-order kinetics","score":0.9160000085830688},{"id":"https://openalex.org/keywords/thioaldehydes","display_name":"thioaldehydes","score":0.4519999921321869},{"id":"https://openalex.org/keywords/carbonyl-rearrangement","display_name":"carbonyl rearrangement","score":0.4050000011920929}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9151754379272461},{"id":"https://openalex.org/C117633835","wikidata":"https://www.wikidata.org/wiki/Q5280165","display_name":"Diradical","level":4,"score":0.9139490127563477},{"id":"https://openalex.org/C58590140","wikidata":"https://www.wikidata.org/wiki/Q306614","display_name":"Sigmatropic reaction","level":2,"score":0.7760105133056641},{"id":"https://openalex.org/C2776981874","wikidata":"https://www.wikidata.org/wiki/Q150717","display_name":"Decane","level":2,"score":0.6777337789535522},{"id":"https://openalex.org/C160434732","wikidata":"https://www.wikidata.org/wiki/Q2611095","display_name":"Thermal decomposition","level":2,"score":0.5989375114440918},{"id":"https://openalex.org/C2780471494","wikidata":"https://www.wikidata.org/wiki/Q146505","display_name":"Solvent","level":2,"score":0.5420393347740173},{"id":"https://openalex.org/C148898269","wikidata":"https://www.wikidata.org/wiki/Q1108792","display_name":"Kinetics","level":2,"score":0.48888033628463745},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.4631796181201935},{"id":"https://openalex.org/C75473681","wikidata":"https://www.wikidata.org/wiki/Q188651","display_name":"Photochemistry","level":1,"score":0.4255245625972748},{"id":"https://openalex.org/C147597530","wikidata":"https://www.wikidata.org/wiki/Q369472","display_name":"Computational chemistry","level":1,"score":0.37755054235458374},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.21690437197685242},{"id":"https://openalex.org/C62520636","wikidata":"https://www.wikidata.org/wiki/Q944","display_name":"Quantum mechanics","level":1,"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/C33062035","wikidata":"https://www.wikidata.org/wiki/Q3296863","display_name":"Singlet state","level":3,"score":0.0},{"id":"https://openalex.org/C181500209","wikidata":"https://www.wikidata.org/wiki/Q215328","display_name":"Excited state","level":2,"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":1,"locations":[{"id":"doi:10.1139/v81-455","doi":"https://doi.org/10.1139/v81-455","is_oa":true,"landing_page_url":"https://doi.org/10.1139/v81-455","pdf_url":"https://cdnsciencepub.com/doi/pdf/10.1139/v81-455","source":{"id":"https://openalex.org/S9189650","display_name":"Canadian Journal of Chemistry","issn_l":"0008-4042","issn":["0008-4042","1480-3291"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","norway-1","poland-40","russia-white-list-3"],"host_organization":"https://openalex.org/P4310312929","host_organization_name":"Canadian Science Publishing","host_organization_lineage":["https://openalex.org/P4310312929"],"host_organization_lineage_names":["Canadian Science Publishing"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Canadian Journal of Chemistry","raw_type":"journal-article"}],"best_oa_location":{"id":"doi:10.1139/v81-455","doi":"https://doi.org/10.1139/v81-455","is_oa":true,"landing_page_url":"https://doi.org/10.1139/v81-455","pdf_url":"https://cdnsciencepub.com/doi/pdf/10.1139/v81-455","source":{"id":"https://openalex.org/S9189650","display_name":"Canadian Journal of Chemistry","issn_l":"0008-4042","issn":["0008-4042","1480-3291"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","norway-1","poland-40","russia-white-list-3"],"host_organization":"https://openalex.org/P4310312929","host_organization_name":"Canadian Science Publishing","host_organization_lineage":["https://openalex.org/P4310312929"],"host_organization_lineage_names":["Canadian Science Publishing"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Canadian Journal of Chemistry","raw_type":"journal-article"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320334593","display_name":"Natural Sciences and Engineering Research Council of Canada","ror":"https://ror.org/01h531d29"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W2073680201.pdf","grobid_xml":"https://content.openalex.org/works/W2073680201.grobid-xml"},"referenced_works_count":2,"referenced_works":["https://openalex.org/W629472250","https://openalex.org/W2942715137"],"related_works":["https://openalex.org/W2019382800","https://openalex.org/W2791870602","https://openalex.org/W2949119698","https://openalex.org/W1999531520","https://openalex.org/W2065836378","https://openalex.org/W2120285409","https://openalex.org/W2054154875","https://openalex.org/W2083541660","https://openalex.org/W2006136990","https://openalex.org/W2170791846"],"abstract_inverted_index":{"2,2-Bis(ethylthio)-3,3-dimethyl-4-pentenal":[0],"was":[1,36],"found":[2,37],"to":[3,6,38],"quantitatively":[4],"isomerize":[5],"2,2-bis(ethylthio)-5-methyl-4-hexenal":[7],"over":[8],"a":[9,22,69],"wide":[10],"temperature":[11],"range":[12],"(130\u2013170":[13],"\u00b0C).":[14],"This":[15],"rearrangement":[16],"can":[17],"formally":[18],"be":[19,30],"regarded":[20],"as":[21],"[1,3]":[23],"sigmatropic":[24],"shift.":[25],"The":[26,43],"reaction,":[27],"which":[28],"could":[29],"conveniently":[31],"monitored":[32],"by":[33],"1Hmr":[34],"spectroscopy,":[35],"obey":[39],"first":[40],"order":[41],"kinetics.":[42],"substantial":[44],"positive":[45],"entropy":[46],"of":[47],"activation":[48],"(+":[49],"61.5":[50],"J":[51],"deg\u22121":[52],"mol\u22121)":[53],"for":[54],"the":[55,58],"reaction":[56],"and":[57],"negligible":[59],"solvent":[60],"effect":[61],"(decane":[62],"vs.":[63],"DMF)":[64],"are":[65],"both":[66],"consistent":[67],"with":[68],"proposed":[70],"diradical":[71],"pathway.":[72]},"counts_by_year":[{"year":2024,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-06-24T00:00:00"}
