Abstract
Whereas elimination of β-piperidinoethyl phenyl sulfone (I) has not been observed, the Hoffmann exhaustive methylation of its methoiodide II in contrast proceeds very rapidly. Phenyl vinyl sulfone (III) formed in the reaction reacts with hydroxyl ions at pH > 12 (k 1 = 6·21 mol−1 s−1). The behaviour of various carbonyl and sulfonyl compounds is compared.
Part VII: This Journal 30, 4316 (1965).
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References
Hordk V., Michl J., Zuman P.: Tetrahedron Letters 21, 744 (1961).
Zuman P., Hordk V.: This Journal 27, 187 (1962).
Cdrsky P., Zuman P., Hordk V.: This Journal 29, 3044 (1964).
Zuman P., Krupicka J.: This Journal 23, 598 (1958); Chem. listy 51, 424 (1957).
Fdldeak S., Matkovics B., Porszasz J.: Acta Phys. Chem. Univ. Szeged 6, 102 (1960).
Ford-Moore A. H., Peters R. A., Wakelin R. W.: J. Chem. Soc. 1949, 1754.
Namfara T.: J. Pharm. Soc. Japan 74, 13 (1954).
Kranzlein G., Heyna J., Schumacher W.: German Pat. 842,198; Chem. Abstr. 47, 11244 (1953).
Johnson C. W., Overberger C. G., Seagers W. J.: J. Am. Chem. Soc. 75, 1495 (1953).
Majranovskij S. G., Neiman M. B.: Dokl. Akad. Nauk SSSR 87, 805 (1953).
Levin E. S., Sestov A. P.: Dokl. Akad. Nauk SSSR 96, 999 (1954).
Horner L., Nickel H.: Chem. Ber. 89, 1681 (1956).
Drushel H. V., Miller J. F.: Anal. Chem. 30, 1271 (1958).
Bowers R. C., Russell H. D.: Anal. Chem. 32, 405 (1960).
Sawicki E., Hauser T. R., Stanley T. W., Elbert W.: Anal. Chem. 33, 93 (1961).
Pasternak R.: Helv. Chim. Acta 31, 753 (1948).
Cdrsky P., Zuman P., Honik V.: This Journal 30, 4316 (1965).
Arnett E. M. in the book: Progress in Physical Organic Chemistry, Vol. 1 (S. G. Cohen, A. Streitwieser, R. W. Taft, Eds), p. 380, 390. Wiley, New York 1963.
Michl J.: Thesis. Charles University, Prague 1961.
Backer H. J., Jong G. J.: Rec. Trav. Chim. 70, 377 (1951).
Truce W. E., Wellisch E.: J. Am. Chem. Soc. 74, 2881 (1952).
Truce W. E., Lewy A. J.: J. Am. Chem. Soc. 83, 4641 (1961).
Prochazka M.: Thesis. Charles University, Prague 1965.
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On the 60th birthday of Academician R. Brdička.
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© 1970 Plenum Publishing Company Ltd.
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Šestáková, I., Zuman, P., Horák, V. (1970). Fission of Activated Carbon-Nitrogen and Carbon-Sulfur Bonds. VIII. Elimination of β-Piperidinoethyl Phenyl Sulfone Methoiodide and Reaction of Phenyl Vinyl Sulfone with Hydroxyl Ions. In: Zuman, P. (eds) Topics In Organic Polarography. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-1812-5_16
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DOI: https://doi.org/10.1007/978-1-4684-1812-5_16
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