2007
DOI: 10.5012/bkcs.2007.28.6.917
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Ketene-Forming Elimination Reactions from Aryl Thienylacetates Promoted by R2NH in MeCN. Effects of Base-Solvent and β-Aryl Group

Abstract: have been studied kinetically. The reactions are second-order and exhibit Brönsted β = 0.51-0.62 and |β lg | = 0.47-0.53. Hence, an E2 mechanism is evident. The Brönsted β increased from 0.33 to 0.53 and |β lg | remained nearly the same by the change of the base-solvent from Bz(i-Pr)NH/Bz(i-Pr)NH 2 + in 70 mol% MeCN(aq) to Bz(i-Pr)NH-MeCN, indicating a change to a more symmetrical transition state with similar extents of C β -H and C α -OAr bond cleavage. When the β-aryl group was changed from thienyl to pheny… Show more

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