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Propargyl alcohol ring expansion

Isomerization-iodination of propargylic alcohols. 1-Phenylethynylcyclopen-tanols do not undergo ring expansion on reaction with NIS-PhI(OH)OTs. The phenyl group apparently changes the polarization of the alkyne unit, which favors formation of a-iodo enones. [Pg.194]

The iron(III) chloride-catalyzed ring expansion reaction of 2-azetidinone-tethered alkynols and allenols provides pyrroles or y-lactones, respectively (Scheme 4-351). The proposed mechanism for the pyrrole formation includes a Meyer-Schuster rearrangement of the propargyl alcohol to the corresponding allenyl alcohol, P-lactam ring opening, tautomerization of the allenyl alcohol to the a,P-unsaturated carbonyl compound, and cyclization by attack of the amino group to the ketone under dehydration. ... [Pg.749]

See other pages where Propargyl alcohol ring expansion is mentioned: [Pg.408]    [Pg.351]    [Pg.1073]    [Pg.68]    [Pg.354]    [Pg.354]    [Pg.362]    [Pg.211]    [Pg.128]    [Pg.311]    [Pg.311]    [Pg.269]   
See also in sourсe #XX -- [ Pg.125 ]



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