Regioselective isomerization at carbon atom vicinal to doubly bo

Details Regioselective isomerization at carbon atom vicinal to doubly bo Regioselective isomerization at carbon atom vicinal to doubly bo

1977-12-20

1980-02-26

Gantz, Delbert E.

Chemistry of hydrocarbon compounds

Alicyclic compound synthesis

By double-bond shift

585377, 585664, 585668, 585941, C07C 530, C07C 1320, C07C 2102

Patent

active

041906128

ABSTRACT:
Beta pinene is converted to alpha pinene in liquid sulfur dioxide. The process is a regioselective isomerization of organic compounds having a carbon-carbon double bond at a tertiary carbon atom, by sulfur dioxide-induced allylic rearrangement of a hydrogen atom and/or replacement of a proton in the allylic position by a deuteron. The organic compound is contacted with sulfur dioxide at temperatures between about 0.degree. and 70.degree. C. for a time sufficient to effect such isomerization to a more stable isomer; and if deuteration is to take place D.sub.2 O is provided in the solution.

REFERENCES:
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patent: 3278623 (1966-10-01), Derfer
patent: 3360581 (1967-12-01), Derfer
patent: 3420910 (1969-01-01), Bordenca et al.
Deboer et al., "The Mechanism of Isomerization of Unsat. Fatty Acids by SO.sub.2 ", Kon. Ned. Acad. W. Proc. 50, 1181-1188 (1947).
Kreuzenkamp et al., "The Catalytic Isom. of Cod Liver Oil with SO.sub.2 ", J. Amer. Oil Chemists Soc. (Sep. 1949), pp. 479-481.
Waterman, Steenis & Deboer, "Isom. of Olefinic Double Bonds by SO.sub.2 ", Research Suppl. 583-585 (2-12-1949).
Vohwinkel, "Reaction of Sulfur Dioxide with Vegetable Oils", Farbe U. Lack 65 571-573 (10-1959).

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