133302-95-1Relevant articles and documents
Stereoselective migration of sterically hindered organoboranes in cyclic and acyclic systems. A stereoselective allylic C-H activation reaction
Hupe, Eike,Denisenko, Dmitri,Knochel, Paul
, p. 9187 - 9198 (2007/10/03)
The thermal migration of cyclic and acyclic organoboranes were studied. In most cases, a stereoselective 1,2-dyotropic migration was observed, allowing the stereocontrol of three contiguous chiral centers. Scope and limitations of this thermal migration are presented.
Vinyl Cations, 36. Solvolysis of Cycloalkylidenemethyl and 1-Cyclopenten-1-yl Triflates
Hanack, Michael,Maerkl, Rainer,Martinez, Antonio Garcia
, p. 772 - 782 (2007/10/02)
Cyclohexylidenemethyl triflate (2), cyclobutylidenemethyl triflate (5), 1-cyclopenten-1-yl triflate (7), bicyclohex-2-en-2-yl triflate (9), 1-cyclobutylideneethyl triflate (19), and 2-methyl-1-cyclopenten-1-yl triflate (29) were solvolyzed in solvents of various ionizing power and nucleophilicity and the solvolysis products were identified.The cyclobutylidenealkyl triflates solvolyze via a vinyl cation mechanism involving ion pairs with rearrangement to cyclopentene and cyclopentanone compounds.The 1-cyclopenten-1-yl triflates do not produce vinyl cation intermediates but give only the corresponding ketones via an O - S bond cleavage of the triflate group.