Matches in SemOpenAlex for { <https://semopenalex.org/work/W1753552421> ?p ?o ?g. }
- W1753552421 endingPage "4570" @default.
- W1753552421 startingPage "4562" @default.
- W1753552421 abstract "The unexpected effect of carbon dioxide on halogen–lithium exchange (HLE) reactions of selected haloarenes with tBuLi was investigated. In an aliphatic hydrocarbon solvent (pentane), the HLE does not occur at ca. –70 °C but, surprisingly, pouring the mixture of reactants onto dry ice and subsequent aqueous acidic hydrolysis gave carboxylic acids resulting from the quench of the first-formed aryllithiums with carbon dioxide. This suggests that CO2 acts as a promoter of the HLE and, subsequently, serves as an electrophile to trap the aryllithium intermediates that are generated in situ. Theoretical DFT calculations were used to develop a plausible mechanism for the reaction, which indicates that CO2 is a much weaker donor than tetrahydrofuran (THF) so the cleavage of inert tBuLi cubic tetramers into more reactive solvated dimeric species (tBuLi)2(CO2)4 is disfavored by 42.8 kJ per mol of (tBuLi)4. It is possible that this deaggregation process occurs to some extent when a large excess of CO2 is used." @default.
- W1753552421 created "2016-06-24" @default.
- W1753552421 creator A5004339587 @default.
- W1753552421 creator A5014983009 @default.
- W1753552421 creator A5050008593 @default.
- W1753552421 creator A5086977817 @default.
- W1753552421 date "2014-06-16" @default.
- W1753552421 modified "2023-10-16" @default.
- W1753552421 title "Is Carbon Dioxide Able to Activate Halogen/Lithium Exchange?" @default.
- W1753552421 cites W1503363138 @default.
- W1753552421 cites W1528630605 @default.
- W1753552421 cites W1552526978 @default.
- W1753552421 cites W1963737263 @default.
- W1753552421 cites W1966182479 @default.
- W1753552421 cites W1966663933 @default.
- W1753552421 cites W1970607102 @default.
- W1753552421 cites W1970640306 @default.
- W1753552421 cites W1971275758 @default.
- W1753552421 cites W1975907815 @default.
- W1753552421 cites W1979021751 @default.
- W1753552421 cites W1981736389 @default.
- W1753552421 cites W1984046031 @default.
- W1753552421 cites W1985691018 @default.
- W1753552421 cites W1990767725 @default.
- W1753552421 cites W1992510044 @default.
- W1753552421 cites W1992571925 @default.
- W1753552421 cites W1993397029 @default.
- W1753552421 cites W1994354759 @default.
- W1753552421 cites W1997151511 @default.
- W1753552421 cites W1998896488 @default.
- W1753552421 cites W2002739930 @default.
- W1753552421 cites W2004057173 @default.
- W1753552421 cites W2006874847 @default.
- W1753552421 cites W2007757764 @default.
- W1753552421 cites W2013766231 @default.
- W1753552421 cites W2015990737 @default.
- W1753552421 cites W2020819890 @default.
- W1753552421 cites W2023271753 @default.
- W1753552421 cites W2026754718 @default.
- W1753552421 cites W2036054016 @default.
- W1753552421 cites W2038083805 @default.
- W1753552421 cites W2039036893 @default.
- W1753552421 cites W2039566409 @default.
- W1753552421 cites W2039620063 @default.
- W1753552421 cites W2042720698 @default.
- W1753552421 cites W2044490585 @default.
- W1753552421 cites W2046029785 @default.
- W1753552421 cites W20481363 @default.
- W1753552421 cites W2051064834 @default.
- W1753552421 cites W2056825505 @default.
- W1753552421 cites W2060021367 @default.
- W1753552421 cites W2068617439 @default.
- W1753552421 cites W2070694619 @default.
- W1753552421 cites W2070770306 @default.
- W1753552421 cites W2081407410 @default.
- W1753552421 cites W2084749145 @default.
- W1753552421 cites W2085909874 @default.
- W1753552421 cites W2086957099 @default.
- W1753552421 cites W2096113724 @default.
- W1753552421 cites W2107229170 @default.
- W1753552421 cites W2109372033 @default.
- W1753552421 cites W2148096262 @default.
- W1753552421 cites W2148989718 @default.
- W1753552421 cites W2151736521 @default.
- W1753552421 cites W2164462170 @default.
- W1753552421 cites W2312832890 @default.
- W1753552421 cites W2326826319 @default.
- W1753552421 cites W2949832278 @default.
- W1753552421 cites W2951451753 @default.
- W1753552421 cites W2953026715 @default.
- W1753552421 cites W4242160608 @default.
- W1753552421 cites W942313901 @default.
- W1753552421 doi "https://doi.org/10.1002/ejoc.201402320" @default.
- W1753552421 hasPublicationYear "2014" @default.
- W1753552421 type Work @default.
- W1753552421 sameAs 1753552421 @default.
- W1753552421 citedByCount "8" @default.
- W1753552421 countsByYear W17535524212015 @default.
- W1753552421 countsByYear W17535524212016 @default.
- W1753552421 countsByYear W17535524212017 @default.
- W1753552421 countsByYear W17535524212020 @default.
- W1753552421 countsByYear W17535524212023 @default.
- W1753552421 crossrefType "journal-article" @default.
- W1753552421 hasAuthorship W1753552421A5004339587 @default.
- W1753552421 hasAuthorship W1753552421A5014983009 @default.
- W1753552421 hasAuthorship W1753552421A5050008593 @default.
- W1753552421 hasAuthorship W1753552421A5086977817 @default.
- W1753552421 hasConcept C134018914 @default.
- W1753552421 hasConcept C161790260 @default.
- W1753552421 hasConcept C178790620 @default.
- W1753552421 hasConcept C178907741 @default.
- W1753552421 hasConcept C179104552 @default.
- W1753552421 hasConcept C185592680 @default.
- W1753552421 hasConcept C2776701986 @default.
- W1753552421 hasConcept C2777207669 @default.
- W1753552421 hasConcept C2778541603 @default.
- W1753552421 hasConcept C2780263894 @default.
- W1753552421 hasConcept C2780471494 @default.