75611-67-5Relevant articles and documents
A mechanistic study of the Lewis base-directed cycloaddition of 2-pyrones and alkynylboranes
Crépin, Damien F.P.,Harrity, Joseph P.A.,Jiang, Julong,Meijer, Anthony J.H.M.,Nassoy, Anne-Chloé M.A.,Raubo, Piotr
, p. 8642 - 8653 (2014)
Significant rate enhancements in the Diels-Alder reaction of alkynes and 2-pyrones bearing a Lewis basic group are observed when a combination of alkynyltrifluoroborates and BF3·OEt2 is used. This process generates functionalized aromatic compounds with complete regiocontrol. The observed rate enhancement was studied by density functional theory methods and appears to originate from coordination of the diene substrate to a mixture of alkynylborane intermediates, followed by a Lewis acid-mediated product equilibration step. Evidence for this mechanism is presented, as is the enhanced promotion of the cycloaddition via the use of alternative Lewis acid promoters.
A mild benzannulation through directed cycloaddition reactions
Kirkham, James D.,Butlin, Roger J.,Harrity, Joseph P. A.
supporting information; experimental part, p. 6402 - 6405 (2012/07/28)
Simple as ABC: Alkynyl borane cycloadditions can be substrate-directed to assemble aromatic difluoroboranes within an extremely mild and efficient reaction manifold compared to that of traditional methods (see scheme). The aromatic boranes are readily transformed into a range of useful products. Copyright
THE QUEEN RECOGNITION PHEROMONE OF SOLENOPSIS INVICTA, PREPARATION OF (E)-6-(1-PENTENYL)-2H-PYRAN-2-ONE.
Rocca, J. R.,Tumlinson, J. H.,Glancey, B. M.,Lofgren, C. S.
, p. 1889 - 1892 (2007/10/02)
The title compound, I, prepared in five steps via four known α-pyrones, is responsible, in part, for "queen recognition" by red imported fire ant workers.IR, NMR and MS data are presented.