Method for opening the gem dicyano epoxides and the formation of compounds therefrom
AssigneeCentre National De La Recherche Scientifique
InventorsAlbert L. F. Robert, Jean-Luc Guinamant, Sylvie C. A. Jaguelin
Life of this patent
Estimating the term…
Abstract
The invention relates to a method for opening the ring of gem dicyanepoxides comprising reacting a gem dicyanepoxide with a mononucleophilic compound in the presence of a hydrohalic acid or a weakly nucleophilic acid.
Claims8
A process for preparing an ester of arylacetic acid comprising reacting an alcohol with a gem dicyanoepoxide, wherein one ring carbon atom bears an aryl group and a hydrogen atom in the presence of hydroiodic acid.
A process for preparing alpha-alkoxy arylactic esters comprising reacting an alcohol with a gem dicyanoepoxide in which a ring carbon atom bears an aryl group and a hydrogen atom in the presence of a weakly nucleophilic acid.
The process for the preparation of the ester of arylacetic acid of the formula ##STR26## which comprises reacting a gem dicyanoepoxide of the formula ##STR27## with a lower alkanol in the presence of hydrobromic acid, hydrochloric aid or hydrofluoric acid, wherein
- R.sub.1 is aryl;
- R.sub.2 is H or CH.sub.3 ;
- X is Br, Cl or F;
- and
- R' is lower alkyl.
A process for preparing ##STR28## which comprises reacting a gem dicyanoepoxide of the formula ##STR29## with water in the presence of hydrobromic acid wherein R.sub.1 is aryl.
The process for preparing .alpha.-halogenated amides of the formula ##STR30## which comprises reacting a gem dicyanoepoxide of the formula ##STR31## with an amine of the formula R' NH.sub.2 in the presence of HX wherein R.sub.1 is pClC.sub.6 H.sub.4, R.sub.2 is H, X is Br and R' is CH.sub.3 CH.sub.2 ;
- R.sub.1 is pClC.sub.6 H.sub.4, R.sub.2 is H, X is Br and R' is CH.sub.3 ;
- R.sub.1 is C.sub.6 H.sub.5, R.sub.2 is H, X is Cl and R' is CH.sub.3 ;
- R.sub.1 is pClC.sub.6 H.sub.4, R.sub.2 is H, X is Cl and R' is C.sub.6 H.sub.5 ;
- R.sub.1 is pClC.sub.6 H.sub.4, R.sub.2 is H, X is Cl and R' is CH.sub.3 CH.sub.2 ;
- R.sub.1 is pMeC.sub.6 H.sub.4, R.sub.2 is H, X is F and R' is H;
- R.sub.1 is pMeC.sub.6 H.sub.4, R.sub.2 is H, X is Cl and R' is CH.sub.2 CH.sub.2 OH;
- R.sub.1 is pClC.sub.6 H.sub.4, R.sub.2 is H, X is Cl and R' is CH.sub.2 CH.sub.2 Cl;
- R.sub.1 is pNO.sub.2 C.sub.6 H.sub.4, R.sub.2 is H, X is Cl and R' is CH.sub.2 CH.sub.2 Cl;
- R.sub.1 is C.sub.6 H.sub.5, R.sub.2 is H, X is Cl and R' is CH.sub.2 CH.sub.2 Cl;
- or
- R.sub.1 is pClC.sub.6 H.sub.4, R.sub.2 is H, X is Cl and R' is CH.sub.2 CH.sub.2 SCN.
The process for forming an arylacetic acid ester of the formula ##STR32## which comprises reacting a gem dicyanoepoxide of the formula ##STR33## with an alcohol of the formula ROH in the presence of p-toluenesulfonic acid, wherein
- Ar is phenyl, R is C.sub.2 H.sub.5 ;
- AR is phenyl, R is (CH.sub.3).sub.2 CH;
- Ar is pNO.sub.2 C.sub.6 H.sub.4, R is C.sub.2 H.sub.5 or
- Ar is pClC.sub.6 H.sub.4, R is C.sub.2 H.sub.5.
Dependencies are inferred from the claim text.