23171-85-9Relevant articles and documents
Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes
Zhou, Hongying,Campbell, E. Joseph,Nguyen, SonBinh T.
, p. 2229 - 2231 (2001)
(Matrix presented) Imidazolinium salts and their N-heterocyclic carbene (NHC) derivatives catalyze the alkylation of a variety of meso epoxides in the presence of triethylaluminum (yield = 70-90%), under mild conditions. Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization side reactions under extended reaction time. Preformed NHC·AIEt3 complexes and Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.
Fragmentierungsreaktionen an Carbonylverbindungen mit β-staendigen elektronegativen Substituenten, XXXIII 3-Oxatricyclo1,4>undec-4-en, ein stark gespannter Vierring-Enolether
Gerdes, Hero,Javeri, Shailaja,Marschall, Helga
, p. 1907 - 1920 (2007/10/02)
The behaviour of β-keto tosylates against nucleophiles has been investigated.The keto tosylate 6 underwent intramolecular cyclization with KOtBu in ether to produce exclusively the four-membered O-alkylated product 18 (the title compound).The substitution products 5 or 7 are obtained from 6 with NaOMe in methanol or KCN in DMSO, resp.Reaction of 6 with MeLi yielded the diol 13.The keto tosylate 31 reacted with MeLi analogously to form the diol 28, whereas with MeMgI a mixture of the Grob fragmentation product 33 and the alcohol 32 (via 28 by H2O elimination) was produced.Similarly keto tosylate 22b and MeMgI yielded the alcohol 27. - The non-enolizable keto tosylate 44 undergoes very slow reaction wih NaOH/MeOH to produce 41, 42, and 45 in low yield.
