Journal of Organic Chemistry p. 3677 - 3682 (1991)
Update date:2022-07-30
Topics:
Murray, Robert W.
Shiang, Dawn L.
Singh, Megh
The reaction of dimethyldioxirane (1) with 4,4-dimethyl-2,3-dihydro-γ-pyran (2) gives the derived epoxide.Measured secondary deuterium isotope effects indicate that there is a greater degree of rehybridization at the β position (5-carbon) than at the α position (6-carbon) in the transition state leading to epoxide.The results are compared to those reported earlier in which 2 was oxidized by singlet oxygen to give the dioxetane.
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