Direct sulfonylation of lithiated alkyl phosphonates with benzenesulfonyl fluoride; Facile method for preparation of α-sulfonyl alkyl phosphonates and vinyl sulfones

Synthetic Communications

Volumn 28, Issue 7, 1998, Pages 1253-1256

  Jang, Won Bum ^a   Jeon, Hyoung Joon ^a   Oh, Dong Young ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; SULFONE DERIVATIVE;

CATALYSIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 0002921715     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808005967     Document Type: Review

References (11)

1. Utilities for α-sulfonyl phosphonates, see: (a) Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A., Synthesis, 1975, 278. (b) Ellingsen, P. O.; Undheim, K., Acta Chem. Scand., 1979, B33, 528. (c) de Jong, B. E.; de Koning, H.; Huisman, H. O., Recl. Trav. Chim. Pays-Bas, 1981, 100, 410. (d) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B., Tetrahedron Lett., 1988, 29, 693. (e) McCarthy, J. R.; Matthew, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T., Tetrahedron Lett., 1990, 31, 5449.
2. Utilities for α-sulfonyl phosphonates, see: (a) Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A., Synthesis, 1975, 278. (b) Ellingsen, P. O.; Undheim, K., Acta Chem. Scand., 1979, B33, 528. (c) de Jong, B. E.; de Koning, H.; Huisman, H. O., Recl. Trav. Chim. Pays-Bas, 1981, 100, 410. (d) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B., Tetrahedron Lett., 1988, 29, 693. (e) McCarthy, J. R.; Matthew, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T., Tetrahedron Lett., 1990, 31, 5449.
3. Utilities for α-sulfonyl phosphonates, see: (a) Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A., Synthesis, 1975, 278. (b) Ellingsen, P. O.; Undheim, K., Acta Chem. Scand., 1979, B33, 528. (c) de Jong, B. E.; de Koning, H.; Huisman, H. O., Recl. Trav. Chim. Pays-Bas, 1981, 100, 410. (d) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B., Tetrahedron Lett., 1988, 29, 693. (e) McCarthy, J. R.; Matthew, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T., Tetrahedron Lett., 1990, 31, 5449.
4. Utilities for α-sulfonyl phosphonates, see: (a) Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A., Synthesis, 1975, 278. (b) Ellingsen, P. O.; Undheim, K., Acta Chem. Scand., 1979, B33, 528. (c) de Jong, B. E.; de Koning, H.; Huisman, H. O., Recl. Trav. Chim. Pays-Bas, 1981, 100, 410. (d) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B., Tetrahedron Lett., 1988, 29, 693. (e) McCarthy, J. R.; Matthew, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T., Tetrahedron Lett., 1990, 31, 5449.
5. Utilities for α-sulfonyl phosphonates, see: (a) Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A., Synthesis, 1975, 278. (b) Ellingsen, P. O.; Undheim, K., Acta Chem. Scand., 1979, B33, 528. (c) de Jong, B. E.; de Koning, H.; Huisman, H. O., Recl. Trav. Chim. Pays-Bas, 1981, 100, 410. (d) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B., Tetrahedron Lett., 1988, 29, 693. (e) McCarthy, J. R.; Matthew, D. P.; Edwards, M. L.; Stemerick, D. M.; Jarvi, E. T., Tetrahedron Lett., 1990, 31, 5449.
6. Utilities for vinyl sulfones, see: Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon Press: Oxford, 1993; Chap. 4.
7. Posner, G. H.; Brunelle, D. J., J. Org. Chem., 1972, 37, 3547.
8. (a) Lee, J. W.; Oh, D. Y., Synth. Commun., 1989, 19, 2209.
9. (b) Lee, J. W.; Oh, D. Y., Synth. Commun., 1990, 20, 273.
10. Paquettte, L. A. Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: Chichester, 1995; Volume 1 pp. 282.
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