3446
F. Grellepois, C. Portella
PAPER
(16) (a) Strukul, G. Catalytic Oxidations with Hydrogen
plete, 35% aq H2O2 soln (2 mmol, 2 equiv) was added dropwise to
the mixture and vigorous stirring was continued for 2 min. The mix-
ture was then diluted with CH2Cl2 and washed with brine and water.
The organic layer was dried (MgSO4), filtered, and concentrated un-
der reduced pressure. The residue was purified on silica gel to afford
the ester.
Peroxide as Oxidant; Kluwer Academic: Dordrecht, 1992.
(b) Burke, S. D.; Danheiser, R. L. Handbook of Reagents for
Organic Synthesis: Oxidizing and Reducing Agents; Wiley:
Chichester, 1999, 174–178.
(17) For the oxidation of thiols into disulfides with alkaline
hydrogen peroxide, see: (a) Price, C. C.; Stacy, G. W. Org.
Synth., Coll. Vol. III; John Wiley & Sons: London, 1955, 86.
(b) Pascal, I.; Tarbell, D. S. J. Am. Chem. Soc. 1957, 79,
6015. (c) Hesse, J. E.; Truby, F. K. Chem. Ind. (London)
1965, 680.
(18) Aqueous hydrogen peroxide could be replaced by solid
urea–hydrogen peroxide adduct (UHP). Under these
conditions, acid 4 was isolated in 88% yield.
(19) All aliquots were acidified before analysis by GC/MS.
Intermediates were identified by comparison of analytical
data (tR, MS peaks) with those of authentic samples of
dithioester 3, acid 4, ester 5, thiolester 6, thionoester 7,
sulfine 8, and dibenzyl disulfide.
(20) For a study of the mechanism of the conversion of
thioamides into amides with hydrogen peroxide at various
pH see: Cashman, J. R.; Hanzlik, R. P. J. Org. Chem. 1982,
47, 4645.
(21) Zwanenburg, B.; Thys, L.; Strating, J. Tetrahedron Lett.
1967, 8, 3453.
(22) Oxathiiranes have already been postulated as intermediates
for the rearrangement of dithioesters into dithioperoxyesters,
see: Metzner, P.; Pham, T. N. J. Chem. Soc., Chem.
Commun. 1988, 390.
(23) Snyder, J. P. J. Am. Chem. Soc. 1974, 96, 5005.
(24) Hu, N. X.; Aso, Y.; Otsubo, T.; Ogura, F. Tetrahedron Lett.
1986, 27, 6099.
(25) Mohammadpoor-Baltork, I.; Memarian, H. R.; Bahrami, K.
Monatsh. Chem. 2004, 135, 411.
References
(1) For a review on the conversion of C=S into C=O, see:
Corsaco, A.; Pistara, V. Tetrahedron 1998, 54, 15027.
(2) For reviews on the preparation of dithioesters, see:
(a) Ramadas, S. R.; Srinisavan, P. S.; Ramachandran, J.;
Sastry, V. V. S. K. Synthesis 1983, 605. (b) Metzner, P.;
Thuillier, A. Sulfur Reagents in Organic Synthesis;
Academic Press: London, 1994. (c) See also: Abrunhosa, I.;
Gulea, M.; Masson, S. Synthesis 2004, 928; and references
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(4) Jorgensen, K. A.; El-Wassimy, M. T. M.; Lawesson, S. O.
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(8) Alper, H.; Kwiatkowska, C.; Petrignani, J. F.; Sibtain, F.
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Tetrahedron 1991, 47, 6275.
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(15) For a-CF3 carboxylic acids, see for example: Hiyama, T.
Organofluorine Compounds: Chemistry and Applications;
Springer Verlag: Berlin, 2000.
(26) Pirkle, W. H.; Sowin, T. J. J. Org. Chem. 1987, 52, 3011.
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(28) El-Wassimy, M. T. M.; Jorgensen, K. A.; Lawesson, S. O.
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(31) Despite the fact that only 1 equiv of base is required, using a
larger amount reduced the reaction time (1 h instead of 15 h).
(32) Aqueous hydrogen peroxide could be replaced by solid
urea–hydrogen peroxide adduct (UHP). Under these
conditions, ester 5 was isolated in 50% yield.
(33) (a) Cazes, B.; Julia, S. Tetrahedron Lett. 1978, 19, 4065.
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Synthesis 2008, No. 21, 3443–3446 © Thieme Stuttgart · New York