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The [4+2] cycloaddition reaction of vinylnitroso compounds with electron-rich alkenes furnishes 5,6-dihydro-4 H-1,2oxazines ( 1). The N-O bond of 1,2-oxazines can be reductively cleaved to obtain hydroxyketones, while C-O bond of 1,2-oxazines can be cleaved under the acidic or thermal conditions. These reactions have been utilized to prepare pyrroles, 2 pyrrolidine, pyridines, 4 γ -lactones, 5 and so on. Herein we would like to report the expansion of [4+2] cycloaddition reaction of vinylnitroso compounds derived from α-halooximes or α,α-dihalooximes toward the preparation of cyclic ethers via 2,6-dioxa-3-azabicycloalkenes.

Synthetic Utilization of 2,6-Dioxa-3-azabicycloalkenes toward Cyclic Ethers