Tandem 1,5-hydrogen transfer and decarbonylation in the flash vacuum pyrolysis of 5-vinyl-3-methyl-1,2-dioxane

Bloodworth, A. J.; Curtis, Richard J.

doi:10.1039/c39890001674

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ChemInform Abstract: Tandem 1,5‐Hydrogen Transfer and Decarbonylation in the Flash Vacuum Pyrolysis of 5‐Vinyl‐3‐methyl‐1,2‐dioxane.

Bloodworth¹,

Curtis²

1990

ChemInform

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047ChemInform Abstract Treatment of the unsaturated hydroperoxide (I) with mercury(II) nitrate results in the formation of cycloperoxymercurials which are demetalated by reduction with sodium borohydride in the presence of a base to give the 1,2-dioxanes (II). (IIa) undergoes rearrangement on flash vacuum pyrolysis, producing the hydroxymethylhexanone (IIIa), whereas the 1,2-dioxane (IIb) yields a mixture of (IIIb) and the fragmentation products (IVb), (Vb), and (VIb). Pyrolysis of the 1,2-dioxanes (IIc) and (IId) yields predominantly the hydroxytetrahydrofurans (VIIa) and (VIIb). When the methylvinyldioxane (IIe) is pyrolyzed, 1,5H-transfer and decarbonylation take place to give the trans-hexenol (X).

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