Concepedia

Oxidations of 3-alkenyltetronic acids with dimethyldioxirane (DMD) and air: regioselectivity and formation of a spirotricyclic hemiketal endoperoxide lactone

Rainer Schobert, Sven Siegfried, J. Weingartner, M. Nieuwenhuyzen

Journal of the Chemical Society Perkin Transactions 1 · 2001 · 14 citations · 9 references

DOI

Concepts

Abstract

The endocyclic CC bond of 3-allyltetronic acid 1 can be selectively oxidised with dimethyldioxirane to give 3-allyl-3-hydroxydihydrofuran-2,4-dione 2 while 3-exo-alkylidenedihydrofuran-2,4-diones 9 are rapidly autooxidised to furnish the spirotricyclic hemiketal endoperoxide lactones 10.

References

9

Synthesis of isocoumarins, dihydroisocoumarins, and isoquinolones via .pi.-allylnickel halide and .pi.-olefin-palladium complexes

D. E. KORTE, Louis S. Hegedus, Ronald K. Wirth · The Journal of Organic Chemistry · 1977 · 131 citations

, , +8

Oxidations of Acyclic Alkenes

Dale E. Van Sickle, Frank R. Mayo, Richard M. Arluck et al. · Journal of the American Chemical Society · 1967 · 71 citations

, , +7

A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides

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, , +10

THE INDUCED DECOMPOSITION OF <i>tert</i>-BUTYL HYDROPEROXIDE

R. Hiatt, John Clipsham, Teunis Visser · Canadian Journal of Chemistry · 1964 · 64 citations

, , +10

The total synthesis of agglomerin A and (±)-carolinic acid. A general method for the preparation of 3-acyl tetronic acids via direct acylation of O-methyl 3-stannyl tetronates

Steven V. Ley, Mark L. Trudell, David J. Wadsworth · Tetrahedron · 1991 · 55 citations

, , +3