Group va ylides and process for preparing same

Details Group va ylides and process for preparing same Group va ylides and process for preparing same

C - Chemistry, Metallurgy

07

F

260/502.5

C07F 9/54 (2006.01) C07F 9/535 (2006.01) C07F 9/70 (2006.01) C07F 9/74 (2006.01) C07F 9/90 (2006.01) C07F 9/92 (2006.01)

Patent

CA 1183155

NOVEL GROUP VA YLIDES AND PROCESS FOR PREPARING SAME Abstract Of The Disclosure There are provided novel Group VA ylides defined by the following Formula I: Image wherein R1, R2, R3, R4 and R5 are either alike or dif- ferent members selected from the group consisting of hy- drogen, 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 carbons atoms, preferably from about two to about 20 car- bon 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 (-SO3-) or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl group carrying a sulfonato group; provided that at least one of R1, R2 and R3 is a sulfonato group or an alkyl, aryl, alkenyl, cyclo- alkyl, aralkyl or alkaryl, as defined above, carrying a sulfonato group; M is sulfur or oxygen, preferably oxygen; and F is phosphorus, arsenic or antimony, preferably phosphor- us. The process for preparing these Group VA ylides comprises reacting a ligand defined by the following for- mula: Image with an alpha-substituted ketone or aldehyde or an alpha- substituted thioketone or thioaldehyde defined by the following formula: Image to obtain the salt defined by the following Formula II: Image wherein R1, R2, R3, R4, R5, F and M are as defined above and X is a halogen radical selected from the group con- sisting of fluorine, chlorine, bromine and iodine, prefer- ably chlorine and bromine, a tosyl group (a toluene sul- fonate group), or an acetate group. This salt is reacted with a base to obtain the novel ylide defined by Formula I.

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