Process for the preparation of nickel ylides containing ylide li

Details Process for the preparation of nickel ylides containing ylide li Process for the preparation of nickel ylides containing ylide li

1980-08-18

1985-07-16

Hines, Robert V.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

556 19, 556 20, 556 21, 556 22, 556 23, 556 30, 502155, C07F 1504

Patent

active

045295549

ABSTRACT:
A process is provided for preparing nickel ylides which are themselves novel compounds defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are either alike or different members selected from the group consisiting 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 or 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; provided that at least one of R.sub.1, R.sub.2 and R.sub.3 is a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl, as defined above, carrying a sulfonato group; M is sulfur or oxygen, preferably oxygen; E is phosphorus, arsenic, antimony or nitrogen, preferably phosphorus; and F is phosphorus, arsenic or antimony, preferably phosphorus. The process comprises reacting a ligand defined by the following formula: ##STR2## with an alpha-substituted ketone or aldehyde or an alpha-substituted thioketone or thioaldehyde defined by the following formula: ##STR3## to obtain the metal salt defined by the following Formula II: ##STR4## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.7, R.sub.8, F and M are as defined above and X is a halogen radical selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably chlorine and bromine, a tosyl group (a tolune sulfonate group), or an acetate group. This metal salt is reacted with a base to obtain the novel ylide defined by the following Formula III: ##STR5## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.7, R.sub.8, F and M are as defined above. This ylide is then reacted with (1) a zero valent nickel compound or any nickel compound convertible to a zero valent nickel compound in situ and (2) a ligand having the formula: ##STR6## wherein R.sub.4, R.sub.5, R.sub.6 and E are as defined above.

REFERENCES:
patent: 2998416 (1961-08-01), Mendel
patent: 3686159 (1972-08-01), Bauer et al.
The Merck Index, 9th Ed., pp. ONR-67 and ONR94 (1976).
Keim et al., "Agnew. Chem." Int. Ed., vol. 17, No. 6, pp. 467-468 (1978).

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