235792-38-8Relevant articles and documents
A Serendipitous Synthesis of Bis-Heterocyclic Spiro 3(2 H)-Furanones
Picado, Alfredo,Li, ShengJian,Dieter, R. Karl
, p. 1391 - 1400 (2016/03/01)
(Z) Enol triflates 6, 11b-d, (E) enol triflate 11e, and phenol triflate 11a, derived from β-keto esters or 2-carboalkoxy phenols, respectively, react with N-Boc 2-lithiopyrrolidine (5a), N-Boc N-methylaminomethyllithium (5b), or 2-lithio-1,3-dithiane (14) to afford 3(2H)-furanones in modest to good yields (38-81%). Product and carbanion reagent studies suggest that the 3(2H)-furanone is formed in a cascade of reactions involving nucleophilic acyl substitution, enolate formation, trifluoromethyl transfer, iminium or sulfenium ion formation, and subsequent ring closure to form the 3(2H)-furanone. The use of 2-lithio-1,3-dithiane affords a cyclic α-keto-S,S,O-orthoester in which the functionality can be selectively manipulated for synthetic applications. (Chemical Equation Presented).
Generation of o-quinone α-carbomethoxymethide by photolysis of methyl 2-hydroxyphenyldiazoacetate in aqueous solution
Chiang,Kresge,Zhu
, p. 1039 - 1042 (2007/10/03)
Flash photolysis of methyl 2-hydroxyphenyldiazoacetate (8) in dilute aqueous perchloric acid solution and acetic acid and biphosphate ion buffers produced a transient species that was identified as o-quinone α-carbomethoxymethide (9). This structural assignment is based upon solvent isotope effects, the form of buffer catalysis, UV absorption maxima, and the identity of decay rate constants with those determined for the transient obtained by flash photolysis of other, more conventional, quinone methide precursors, namely the benzyl alcohol methyl 2-hydroxy mandelate (10) and its acetate, 2′-acetoxy-2-hydroxyphenylacetate (11).
