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Preparation of 2-Methylene-1,3-propanediamide
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Inventors: Haas, Howard C.; Jasne, Stanley J.; Moreau, Robert D.;
Assignee: Polaroid Corporation (Cambridge, MA)
Primary Examiner: Demers; Arthur P.
Assistant Examiner:
Attorney, Agent or Firm: Wasatonic; John J.
A process for preparing 2-methylene-1,3-propanediamide is disclosed which comprises providing a solution of a novel compound of the formula ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 can each independently be lower alkyl of from 1 to 10 carbon atoms, aryl, alkaryl, aralkyl, or halogen and X is an electron-accepting leaving group, in an inert, aprotic organic solvent, and subjecting the compound in solution to .beta.-elimination reaction conditions effective to eliminate the silyl group ##STR2## and the electron-accepting leaving group --X from the compound to form a double bond between those carbon atoms to which the silyl group and the electron-accepting leaving group were bonded, thereby forming 2-methylene-1,3-propanediamide. 2-Methylene-1,3-propanediamide is useful in preparing polymers which can be used in preparing coating compositions, films, and filaments. |
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DETAILED DESCRIPTION OF THE INVENTION Preparation of 2-methylene-1,3-propanediamide tends to be difficult because of the high reactivity of this monomer.
For example, it has been found to be sensitive to protic materials whereby the monomer is derivatized by addition of the protic material across the double bond, e.
g.
, ##STR6## Such derivatization reactions are generally also accompanied by some degree of polymerization of the monomer.
In addition, the monomer has been found to readily undergo anionic and free radical polymerization reactions such that preparation and isolation of the monomer without a substantial degree of concurrent polymerization tends to be difficult.
The present invention provides a novel process for preparing 2-methylene-1,3-propanediamide which is capable of providing the desired monomer in high yield with minimal derivatization or polymerization.
This process has proven to be a particularly advantageous method of preparing this monomer since the high reactivity of the monomer tends to render other potential methods of preparation either impractical or inoperative.
The process of the present invention comprises providing a solution of a compound of the formula ##STR7## where R.
sub.
1, R.
sub.
2 and R.
sub.
3 each can independently be lower alkyl of from 1 to 10 carbon atoms, aryl, alkaryl, aralkyl, or halogen, and X is an electron-accepting leaving group, in an inert, aprotic organic solvent, and subjecting the compound in solution to .
beta.
-elimination reaction conditions effective to eliminate the silyl group ##STR8## and the electron-accepting leaving group --X from the compound to form a double bond between those carbon atoms to which the silyl group and the electron-accepting leaving group were bonded, thereby forming 2-methylene-1,3-propanediamide.
The removal of the silyl group and the electron-accepting leaving group situated .
beta.
thereto from the starting material to form the desired carbon-carbon double bond constitutes a .
beta.
-elimination reaction.
Thus, by the term "
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Nonmetallic Processes 
