Sulfonated group VA ylides and process for preparing same

Details Sulfonated group VA ylides and process for preparing same Sulfonated group VA ylides and process for preparing same

1980-11-24

1983-03-22

Sneed, Helen M. S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260446, 568 9, 568 11, 568 13, 568 14, 568 15, 568 16, 564282, 564291, C07F 970, C07F 972, C07F 990, C07F 950

Patent

active

043775292

ABSTRACT:
There are provided novel sulfonated group Va ylides defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are either alike or different members selected from the group consisting of hydrogen, alkyl radicals having from about one to about 24 carbon atoms, preferably from about one to about 10 carbon atoms; aryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 10 carbon atoms; alkenyl radicals having from about two to about 30 carbon atoms, preferably from about two to about 20 carbon atoms; cycloalkyl radicals having from about three to about 40 carbon atoms, preferably from about three to about 30 carbon atoms; aralkyl and alkaryl radicals having from about six to about 40 carbon atoms, preferably from about six to about 30 carbon atoms; a halogen radical selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably chlorine; a hydroxyl group; an alkoxy or aryloxy group; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl, alkoxy or aryloxy; and a sulfonato group (SO.sub.3.sup.-) or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl group carrying a sulfonato group; M is sulfur or oxygen, preferably oxygen; F is phosphorus, arsenic or antimony, preferably phosphorus; and A is the cationic residue of a base selected from the group consisting of an alkali metal hydroxide, an alkyl or aryl lithium, an alkoxide and a hydrocarbyl-substituted ammonium hydroxide.
The process for preparing these sulfonated ylides comprises sulfonating an ylide defined by the following Formula II: ##STR2## to obtain the sulfonated ylide defined by the following Formula III: ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, F and M are as defined above. The sulfonated ylide is reacted with a base selected from the group consisting of an alkali metal hydroxide, an alkyl or aryl lithium, an alkoxide and a hydrocarbyl-substituted ammonium hydroxide to obtain the ylide defined by Formula I.

REFERENCES:
patent: 3686159 (1972-08-01), Bauer et al.
Gilbert, "Sulfonation and Related Reactions", Interscience Publ., p. 61 (1965).
Nesmeyanov et al., "Sulfonation of Phosphorylides, Sulfobetaines", Dok, Acad. Nauk SSSR, vol. 151, No. 4, pp. 856-858 (1963).

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