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PANGAEA Supplementary Data
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doi:10.1016/S0040-4039(00)83959-3    
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Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.

Oxidative coupling. : III. The duco reaction

J. L. Belletire, * and E. G. Spletzer

Department of Chemistry University of Cincinnati Cincinnati, Ohio 45221 U.S.A.


Received 16 September 1985. 
Available online 8 March 2001.

Abstract

Acylsulfonamide dianions function as efficient synthetic intermediates and are especially suitable for Doubly Unsymmetrical Çarbanion Oxidation.

References

J.L. Belletire, E.G. Spletzer and A.R. Pinhas Tetrahedron Lett. 25 (1984), p. 5969. Abstract | PDF (263 K) | View Record in Scopus | Cited By in Scopus (22)

There is considerable circumstantial evidence that these oxidative coupling reactions may proceed by an electron transfer mechanism. For a recent paper discussing an electron transfer viewpoint regarding enolate alkylations, see E.C. Ashby and J.N. Argyropoulos Tetrahedron Lett. 25 (1984), p. 7. Abstract | PDF (205 K) | View Record in Scopus | Cited By in Scopus (3)

Reaction of both 7a and 7b with more typical electrophiles (e.g. iodomethane and benzyl chloride) led to excellent isolated yields (−90%) of the corresponding C-alkylated products.

For a table of comparative acidities, see: J. March In: Advanced Organic Chemistry, Wiley-Interscience, New York (1985), pp. 220–223 and references therein .

All new compounds gave satisfactory analytical data.

T.K. Schaaf and H.-J. Hess J. Med. Chem. 22 (1979), p. 1340. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (33)

R. Brans and R.J.W. Cremlyn J. Chem. Soc. (C) (1970), p. 225 and references therein . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (0)

Y.-N. Kuo, J.A. Yahner and C.J. Ainsworth J. Am. Chem. Soc. 93 (1971), p. 6321. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)
R.B. Meyer and C.R. Hauser J. Org. Chem. 26 (1961), p. 3183. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (0)
J. Muizer, G. Bruntrup, G. Hartz, U. Kuhl, U. Blaschek and G. Bohrer Chem. Ber. 114 (1981), p. 3701.

16 (R = Ph; R″ = H): Combustion analysis: C; Th, 57.65; Fd, 57.70. H; Th, 4.53; Fd, 5.04. N; Th, 4.20: Fd, 4.16. (b) 16 (R = PhCH2; R″ = H): Combustion Analysis: C; Th, 58.78; Fd, 58.79. H; Th, t.93; Fd, 5M. N; Th, 4.03; Fd, 3.90.

The broad melting point range is due to the presence of stereoisomers.

L.M.X. Lopes, M. Yoshida and O.R. Gottlieb Phytochemistry 22 (1983), p. 1516. Abstract | PDF (276 K) | View Record in Scopus | Cited By in Scopus (37)

P.B. McDoniel and J.R. Cole J. Pharm. Sci. 61 (1972), p. 1992. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (22)


Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 131-134
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