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

1980-11-25

1983-07-19

Sneed, Helen M. S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260446, 568 13, 568 14, 568 15, C07F 972, C07F 974, C07F 990, C07F 950

Patent

active

043943225

ABSTRACT:
There are provided novel Group VA ylides defined by the following Formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 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; 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; and F is phosphorus, arsenic or antimony, preferably phosphorus.
The process for preparing these Group VA ylides 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 salt defined by the following Formula II: ##STR4## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, 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 toluene sulfonate group), or an acetate group. This salt is reacted with a base to obtain the novel ylide defined by Formula I.

REFERENCES:
patent: 2998416 (1961-08-01), Mendel
patent: 3686159 (1972-08-01), Bauer et al.
Kosolapoff et al., Organic Phosphorus Compounds, vol. 3, pp. 97-108, (1972).
Doak et al., Organometallic Compounds of Arsenic, Antimony & Bismuth, John Wiley & Sons, N. Y., pp. 225-227, 343-344, (1970).
Ramirez et al., J. Organic Chem. 22, pp. 41-45, (1957).
Hauser, J. Organic Chem. 27, 43-46, (1962).
Ahrland et al., "The Relative Affinities of Coordinating Atoms for Silver Ion, Part II, Nitrogen, Phosphorous and Arsenic", J. Chem. Soc., pp. 276-288, (1958).

Affiliated with

Also associated with

Rating

Group VA ylides and process for preparing same does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Group VA ylides and process for preparing same, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Group VA ylides and process for preparing same will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-750917