
Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.
J. L. Belletire, * and E. G. Spletzer
Department of Chemistry University of Cincinnati Cincinnati, Ohio 45221 U.S.A.
Received 16 September 1985.
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)
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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)
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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.
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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.
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