{"id":"https://openalex.org/W2051448985","doi":"https://doi.org/10.1002/chem.200903521","title":"Stereodivergent Quaternization of 2\u2010Alkyl\u20102\u2010p\u2010tolylsulfinylacetonitriles: NMR Spectroscopic Evidence of Planar and Pyramidal Benzylic Carbanions","display_name":"Stereodivergent Quaternization of 2\u2010Alkyl\u20102\u2010p\u2010tolylsulfinylacetonitriles: NMR Spectroscopic Evidence of Planar and Pyramidal Benzylic Carbanions","publication_year":2010,"publication_date":"2010-04-21","ids":{"openalex":"https://openalex.org/W2051448985","doi":"https://doi.org/10.1002/chem.200903521","mag":"2051448985","pmid":"https://pubmed.ncbi.nlm.nih.gov/20411540"},"language":"en","primary_location":{"id":"doi:10.1002/chem.200903521","doi":"https://doi.org/10.1002/chem.200903521","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.200903521","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry \u2013 A European Journal","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":null,"display_name":"Jos\u00e9\u2005Luis Garc\u00eda\u2005Ruano","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I63634437","display_name":"Universidad Aut\u00f3noma de Madrid","ror":"https://ror.org/01cby8j38","country_code":"ES","type":"education","lineage":["https://openalex.org/I63634437"]}],"countries":["ES"],"is_corresponding":false,"raw_author_name":"Jos\u00e9\u2005Luis Garc\u00eda\u2005Ruano","raw_affiliation_strings":["Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es","Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es","institution_ids":["https://openalex.org/I63634437"]},{"raw_affiliation_string":"Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5053933721","display_name":"A. M. Mart\u00edn-Castro","orcid":null,"observed_orcids":[]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Ana\u2005M. Mart\u00edn\u2010Castro","raw_affiliation_strings":["Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5030473186","display_name":"Francisco Tato","orcid":"https://orcid.org/0000-0002-5070-1038","observed_orcids":["https://orcid.org/0000-0002-5070-1038"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Francisco Tato","raw_affiliation_strings":["Departamento Quimica Orga\u0301nica, Cantoblanco, 28049 Madrid (Spain),","Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departamento Quimica Orga\u0301nica, Cantoblanco, 28049 Madrid (Spain),","institution_ids":[]},{"raw_affiliation_string":"Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966","institution_ids":[]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5018163909","display_name":"Esther Torrente","orcid":"https://orcid.org/0000-0002-3594-9334","observed_orcids":["https://orcid.org/0000-0002-3594-9334"]},"institutions":[],"countries":[],"is_corresponding":false,"raw_author_name":"Esther Torrente","raw_affiliation_strings":["Departamento Quimica Orga\u0301nica, Cantoblanco, 28049 Madrid (Spain),","Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Departamento Quimica Orga\u0301nica, Cantoblanco, 28049 Madrid (Spain),","institution_ids":[]},{"raw_affiliation_string":"Departamento Quimica Org\u00e1nica, Cantoblanco, 28049 Madrid (Spain), Fax: (+34)\u2009914973966","institution_ids":[]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5028035652","display_name":"Ana M. Poveda","orcid":"https://orcid.org/0000-0001-5060-2307","observed_orcids":["https://orcid.org/0000-0001-5060-2307"]},"institutions":[{"id":"https://openalex.org/I63634437","display_name":"Universidad Aut\u00f3noma de Madrid","ror":"https://ror.org/01cby8j38","country_code":"ES","type":"education","lineage":["https://openalex.org/I63634437"]}],"countries":["ES"],"is_corresponding":false,"raw_author_name":"Ana\u2005M. Poveda","raw_affiliation_strings":["Servicio Interdepartamental de Investigacio\u0301n, Universidad Auto\u0301noma de Madrid, Cantoblanco, 28049 Madrid (Spain)","Servicio Interdepartamental de Investigaci\u00f3n, Universidad Aut\u00f3noma de Madrid, Cantoblanco, 28049 Madrid (Spain)"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Servicio Interdepartamental de Investigacio\u0301n, Universidad Auto\u0301noma de Madrid, Cantoblanco, 28049 Madrid (Spain)","institution_ids":["https://openalex.org/I63634437"]},{"raw_affiliation_string":"Servicio Interdepartamental de Investigaci\u00f3n, Universidad Aut\u00f3noma de Madrid, Cantoblanco, 28049 Madrid (Spain)","institution_ids":["https://openalex.org/I63634437"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":4640,"currency":"USD","value_usd":4640},"apc_paid":null,"fwci":2.0702,"has_fulltext":false,"cited_by_count":25,"citation_normalized_percentile":{"value":0.85392054,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":98},"biblio":{"volume":"16","issue":"21","first_page":"6317","last_page":"6325"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.3337000012397766,"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/T10013","display_name":"Asymmetric Synthesis and Catalysis","score":0.3337000012397766,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.30640000104904175,"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/T12191","display_name":"Physical Organic Chemistry and Reaction Kinetics","score":0.24789999425411224,"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/stereoselective-synthesis","display_name":"stereoselective synthesis","score":0.6840000152587891},{"id":"https://openalex.org/keywords/alkyl-halide-alkylation","display_name":"alkyl halide alkylation","score":0.6200000047683716},{"id":"https://openalex.org/keywords/khmds","display_name":"KHMDS","score":0.6579999923706055},{"id":"https://openalex.org/keywords/18-crown-6-ether","display_name":"18-crown-6 ether","score":0.9340000152587891},{"id":"https://openalex.org/keywords/counterion-effects","display_name":"counterion effects","score":0.7459999918937683}],"concepts":[{"id":"https://openalex.org/C82894169","wikidata":"https://www.wikidata.org/wiki/Q898552","display_name":"Carbanion","level":2,"score":0.9832884073257446},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9194203615188599},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.7108355164527893},{"id":"https://openalex.org/C138716334","wikidata":"https://www.wikidata.org/wiki/Q268477","display_name":"Diastereomer","level":2,"score":0.6231220364570618},{"id":"https://openalex.org/C486523","wikidata":"https://www.wikidata.org/wiki/Q494483","display_name":"Enantiomer","level":2,"score":0.5292030572891235},{"id":"https://openalex.org/C155647269","wikidata":"https://www.wikidata.org/wiki/Q243455","display_name":"Medicinal chemistry","level":1,"score":0.5011343955993652},{"id":"https://openalex.org/C2780407432","wikidata":"https://www.wikidata.org/wiki/Q103230","display_name":"Ether","level":2,"score":0.48623648285865784},{"id":"https://openalex.org/C2777255693","wikidata":"https://www.wikidata.org/wiki/Q410125","display_name":"Crown ether","level":3,"score":0.48013707995414734},{"id":"https://openalex.org/C34814092","wikidata":"https://www.wikidata.org/wiki/Q2268418","display_name":"Counterion","level":3,"score":0.46982812881469727},{"id":"https://openalex.org/C181647583","wikidata":"https://www.wikidata.org/wiki/Q903429","display_name":"Stereoselectivity","level":3,"score":0.4100692868232727},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.38765639066696167},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2586584687232971},{"id":"https://openalex.org/C145148216","wikidata":"https://www.wikidata.org/wiki/Q36496","display_name":"Ion","level":2,"score":0.0818202793598175},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.06965124607086182}],"mesh":[{"descriptor_ui":"D000097","descriptor_name":"Acetonitriles","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D000478","descriptor_name":"Alkylation","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D000838","descriptor_name":"Anions","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D002244","descriptor_name":"Carbon","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D009682","descriptor_name":"Magnetic Resonance Spectroscopy","qualifier_ui":null,"qualifier_name":null,"is_major_topic":true},{"descriptor_ui":"D013237","descriptor_name":"Stereoisomerism","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false}],"locations_count":2,"locations":[{"id":"doi:10.1002/chem.200903521","doi":"https://doi.org/10.1002/chem.200903521","is_oa":false,"landing_page_url":"https://doi.org/10.1002/chem.200903521","pdf_url":null,"source":{"id":"https://openalex.org/S68911691","display_name":"Chemistry - A European Journal","issn_l":"0947-6539","issn":["0947-6539","1521-3765"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["anvur-scientific","cwts-core","dongbi-c","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Chemistry \u2013 A European Journal","raw_type":"journal-article"},{"id":"pmid:20411540","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/20411540","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":"Chemistry (Weinheim an der Bergstrasse, Germany)","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":42,"referenced_works":["https://openalex.org/W63134952","https://openalex.org/W1502209126","https://openalex.org/W1963728305","https://openalex.org/W1964374083","https://openalex.org/W1965253546","https://openalex.org/W1969470048","https://openalex.org/W1984962228","https://openalex.org/W1985358527","https://openalex.org/W1990608904","https://openalex.org/W1990834611","https://openalex.org/W1994433607","https://openalex.org/W1996128658","https://openalex.org/W1996218404","https://openalex.org/W2002140193","https://openalex.org/W2003565760","https://openalex.org/W2017999175","https://openalex.org/W2018052442","https://openalex.org/W2021159498","https://openalex.org/W2029402467","https://openalex.org/W2032942131","https://openalex.org/W2043671979","https://openalex.org/W2048784427","https://openalex.org/W2084585298","https://openalex.org/W2085792772","https://openalex.org/W2085923381","https://openalex.org/W2087047567","https://openalex.org/W2111589261","https://openalex.org/W2119687359","https://openalex.org/W2123469077","https://openalex.org/W2132614735","https://openalex.org/W2133111093","https://openalex.org/W2134659588","https://openalex.org/W2136210947","https://openalex.org/W2171866871","https://openalex.org/W2949327172","https://openalex.org/W2949719082","https://openalex.org/W2949779263","https://openalex.org/W2949790684","https://openalex.org/W2952902444","https://openalex.org/W2953062795","https://openalex.org/W4232140635","https://openalex.org/W4236449917"],"related_works":["https://openalex.org/W2032942131","https://openalex.org/W2073478996","https://openalex.org/W2008796334","https://openalex.org/W3201493811","https://openalex.org/W2048150521","https://openalex.org/W2437992301","https://openalex.org/W2177233037","https://openalex.org/W1984443171","https://openalex.org/W2951387934","https://openalex.org/W4387812283"],"abstract_inverted_index":{"Enantiomerically":[0],"enriched":[1],"alpha,alpha-disubstituted":[2],"phenylacetonitriles":[3],"have":[4],"been":[5,70,86],"readily":[6],"prepared":[7],"by":[8,72,88],"stereoselective":[9],"quaternization":[10],"of":[11,20,24,54,58,122],"2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles":[12],"with":[13,31],"different":[14],"alkylating":[15],"electrophiles":[16],"in":[17,40,119],"the":[18,55,59,62,67,80,102,114,120],"presence":[19,121],"bases.":[21],"The":[22,52],"use":[23],"potassium":[25,115],"hexamethyldisilazane":[26],"(KHMDS)/[18]crown-6":[27],"ether":[28],"and":[29,36,106],"NHMDS":[30],"alkyl":[32],"halides":[33],"afforded":[34],"S,S(S)":[35],"R,S(S)":[37],"diastereoisomers,":[38],"respectively,":[39],"high":[41],"enantiomeric":[42],"purities,":[43],"thus":[44],"providing":[45],"stereodivergent":[46],"processes":[47],"for":[48,79],"synthesizing":[49],"both":[50],"isomers.":[51],"dependence":[53],"stereochemical":[56],"course":[57],"reactions":[60],"on":[61,66],"experimental":[63],"conditions":[64],"(mainly":[65],"counterion)":[68],"has":[69,85],"rationalized":[71],"assuming":[73],"a":[74,97],"planar":[75,109],"or":[76],"pyramidal":[77,99],"structure":[78,100,112],"benzylic":[81,104,116],"carbanions.":[82],"This":[83],"hypothesis":[84],"supported":[87],"NMR":[89],"spectroscopic":[90],"studies,":[91],"which":[92],"permit":[93],"one":[94],"to":[95,101,113],"assign":[96],"chelated":[98],"sodium":[103],"carbanions":[105,117],"an":[107],"almost":[108],"naked":[110],"carbanionic":[111],"generated":[118],"[18]crown-6":[123],"ether.":[124]},"counts_by_year":[{"year":2020,"cited_by_count":2},{"year":2018,"cited_by_count":1},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":3},{"year":2015,"cited_by_count":2},{"year":2014,"cited_by_count":2},{"year":2013,"cited_by_count":5},{"year":2012,"cited_by_count":4}],"updated_date":"2026-11-04T10:54:05.112534","created_date":"2016-06-24T00:00:00"}