ol0c01510_si_001.pdf (1.6 MB)
Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene
journal contribution
posted on 2020-05-21, 18:05 authored by Matthew
S. McVeigh, Andrew V. Kelleghan, Michael M. Yamano, Rachel R. Knapp, Neil K. GargTransient
strained cyclic intermediates have become valuable intermediates
in modern synthetic chemistry. Although silyl triflate precursors
to strained intermediates are most often employed, the instability
of some silyl triflates warrants the development of alternative precursors.
We report the syntheses of silyl tosylate precursors to cyclohexyne,
1,2-cyclohexadiene, and 1,2-cycloheptadiene. The resultant strained
intermediates undergo trapping in situ to give cycloaddition products.
Additionally, the results of competition experiments between silyl
triflates and silyl tosylates are reported.