Synthesis of 1,3-oxathiolane sulfoxide compounds

Details Synthesis of 1,3-oxathiolane sulfoxide compounds Synthesis of 1,3-oxathiolane sulfoxide compounds

1995-09-14

1997-08-05

Dees, Jose' G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 40, 549 30, C07D32706, C07D32704

Patent

active

056544413

ABSTRACT:
A process for the production of a 1,3-oxathiolane sulfoxide of the formula ##STR1## wherein X is an amino group of the formula --NHR, wherein R is hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, nitrophenyl, (C.sub.1 -C.sub.4 alkoxy)phenyl, furfuryl, halophenyl, tolyl, napthyl, biphenyl or hydroxyphenyl; or X is an alkoxy group of the formula --OR.sup.1 wherein R is C.sub.1 -C.sub.6 alkyl,
which process comprises oxidizing a 1,3-oxathiolane of the formula ##STR2## wherein X is as defined above, in the presence of an effective amount of aqueous hydrogen peroxide and a sterically-hindered organoselenium compound of the formula ##STR3## wherein R.sup.2 is aryl, mono-, di- or tri-substituted with C.sub.1 -C.sub.3 alkyl,
to the produce the 1,3-oxathiolane sulfoxide. This process stereoselectively produces the cis stereoisomer of the 1,3-oxathiolane sulfoxide. Additionally, there is disclosed a novel method for the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin compounds using this process.

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patent: 4247707 (1981-01-01), Znotins
Lee et al, "Synthesis of Dihydro-1,4-oxathiins by Rearrangement of 1,3-Oxathiolane Sulfoxides", J. Org. Chem. 51:2789-2795 (1986).
Reich et al, "Seleninic Acids as Catalysts for Oxidations of Olefins and Sulfides Using Hydrogen Peroxide", Synthesis, Apr. 1978, pp. 299-301.
Lee et al, "Sulfenic Acid derived from 1,3-oxathiolane-3-oxide", Taehan Hwahakhoe Chi 31(2): 197-202 (1987) (English language translation).
Lee et al, "Sulfene Acid derived from 1,3-oxathnolane-3-oxide", Chem. Abs. vol. 108. No. 5888d. (1988).

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