74510-34-2Relevant academic research and scientific papers
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.
