Thioimidate N-oxides: nitrones of thio esters
RM Coates, SJ Firsan - The Journal of Organic Chemistry, 1986 - ACS Publications
RM Coates, SJ Firsan
The Journal of Organic Chemistry, 1986•ACS Publications4o, 4b, 4c 5o, R= CH3 (547o) 5b, R= CH3CH2 (55%) 5c, R=(CH3) 2CH (30%) acetate (4a)
and thiopropionate (4b, 71%) were prepared by ferric chloride catalyzed sulfhydrolysis of
ethyl ortho-acetate and orthopropionate. 9 Reaction of isobutyronitrile imino ether
hydrochloride10 with hydrogen sulfide in quinoline11* gave O-methyl thioisobutyrate (4c) in
78% yield. The alkyl series of A-alkylthiohydroxamic acids 5a-c was obtained by
thioacylation of A-methyl-hydroxylamine withthio esters 4a-c in methanol at room …
and thiopropionate (4b, 71%) were prepared by ferric chloride catalyzed sulfhydrolysis of
ethyl ortho-acetate and orthopropionate. 9 Reaction of isobutyronitrile imino ether
hydrochloride10 with hydrogen sulfide in quinoline11* gave O-methyl thioisobutyrate (4c) in
78% yield. The alkyl series of A-alkylthiohydroxamic acids 5a-c was obtained by
thioacylation of A-methyl-hydroxylamine withthio esters 4a-c in methanol at room …
4o, 4b, 4c 5o, R= CH3 (547o) 5b, R= CH3CH2 (55%) 5c, R=(CH3) 2CH (30%) acetate (4a) and thiopropionate (4b, 71%) were prepared by ferric chloride catalyzed sulfhydrolysis of ethyl ortho-acetate and orthopropionate. 9 Reaction of isobutyronitrile imino ether hydrochloride10 with hydrogen sulfide in quinoline11* gave O-methyl thioisobutyrate (4c) in 78% yield. The alkyl series of A-alkylthiohydroxamic acids 5a-c was obtained by thioacylation of A-methyl-hydroxylamine withthio esters 4a-c in methanol at room temperature for 4.5-48 h. 118, 12 S-Alkylation of the A-alkylthiohydroxamic acids was accomplished by reaction with 3 equiv of methyl iodide (3)(a) Lee, T. D.; Keana, JFW J. Org. Chem. 1976, 41, 3237-3241.(b) Ashbum, S. P.; Coates, R. M. Ibid. 1984, 49, 3127-3133.(c) Ashbum, S. P.; Coates, R. M. Ibid. 1985, 50, 3076-3081.(d) Hendrickson, JB; Pearson, DA Tetrahedron Lett. 1983, 24, 4657-4660.(4) Zbaida, S.; Brewer, E., unpublished results cited in ref lb pp 528-529 (5)(a) Kerr, DA; Wilson, DA J. Chem. Soc. C 1970, 1718-1725.(b) Pennings, MLM; Reinhoudt, D. NJ Org. Chem. 1982, 47, 1816-1823.(6) Walter, W.; Schaumann, E. Synthesis 1971, 111-130.(7) Walter, W.; Voss, J. In The Chemistry of Amides·, Zabicky, J., Ed.; Interscience: London, 1970; pp 383-475.(8) S-(Thiobenzoyl) thioglycolic acid (1) is available from Aldrich Chemical Co. It may alsobe prepared by the following literature pro-cedure: Kurzer, F.; Lawson, A. Organic Syntheses, Wiley: New York, 1973; Collect. Vol. V, pp 1046-1049.(9) Ohno, A.; Koizumi, T.; Tsuchihashi, G. Tetrahedron Lett. 1968, 2083-2085.
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