US 4,003,943 A · Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same

Abstract

Trimethylenecyclopropane wherein all six hydrogen atoms are symmetrically substituted with cyano, alkoxycarbonyl or carbacyl groups and which are salt-forming can be made by reacting tetrachlorocyclopropene with the appropriate active methylene compound such as malononitrile, acetyl acetone or ethyl cyanoacetate. Using limited amounts of malononitrile and a tertiary amine, a tetracyanodimethylenecyclopropene substituted with a quaternary ammonium group is obtained, which reacts with other active methylene compounds including the above, nitroalkanes, benzoylacetonitrile, benzenesulfonylacetonitrile, and dialkyl sulfones to form unsymmetrical substituted trimethylenecyclopropane. The neutral compounds are useful as organic oxidants. Their radical anion salts are useful as organic conductors and as dyes, and the dianion salts are useful as image formers on transparent films or on opaque substrates.

Claims8

Dependent claims

A compound having the formula:

##STR29## wherein X and Y are selected from cyano,-COO (lower alkyl) or --CO (lower alkyl);
L and Q are selected pairwise from phenyl and cyano, phenacetyl and cyano or benzenesulfonyl and cyano;
and M.sup.+ is one equivalent of an inert cation.

Dependencies are inferred from the claim text.

Facts

Application

05/663,102Filed 2 Mar 1976 · division

Priority

20 Dec 1974

Granted

18 Jan 1977

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07C 49/21
Unsaturated compounds containing keto groups bound to acyclic carbon atoms: containing rings other than six-membered aromatic rings
C07C 45/68
By isomerisation; by change of size of the carbon skeleton: by increase in the number of carbon atoms
C07D 213/20
Containing only one pyridine ring: quaternary compounds thereof
G03C 1/73
Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705: containing organic compounds

Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same

Life of this patent

Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same

Life of this patent

Abstract

Claims8