US4003943A
Expired / Lapsed
US
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Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same
Assignee: EIDP Inc
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Filing: 1976-03-02
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Granted: 1977-01-18
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Expires: 1996-03-02
Abstract
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.
Inventors
- 👤 Tadamichi Fukunaga
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 03:34
CPC Classifications
C; C07; C07C; C07C49/00; C07C49/20; C07C49/21; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/06; C07D213/16; C07D213/20; G; G03; G03C; G03C1/00; G03C1/72; G03C1/73
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
46 words
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 + is one equivalent of an inert cation.
Claim 2
Dependent Claim
46 words
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 + is one equivalent of an inert cation.
Claim 3
Dependent Claim
12 words
The compound of claim 1 wherein each X and Y is cyano.
Claim 4
Dependent Claim
48 words
A compound having the formula: ##STR30##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 benzene sulfonyl and cyano; and M + is one equivalent of an inert cation.
Claim 5
Dependent Claim
48 words
A compound having the formula: ##STR30##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 benzene sulfonyl and cyano; and M + is one equivalent of an inert cation.
Claim 6
Dependent Claim
12 words
The compound of claim 3 wherein each X and Y is cyano.
Claim 7
Dependent Claim
38 words
A compound having the formula: ##STR31##wherein X and Y are selected from cyano, --COO (lower alkyl) or --CO (lower alkyl); and L and Q are selected pairwise from phenyl and cyano, phenacetyl and cyano or benzenesulfonyl and cyano.
Claim 8
Dependent Claim
38 words
A compound having the formula: ##STR31##wherein X and Y are selected from cyano, --COO (lower alkyl) or --CO (lower alkyl); and L and Q are selected pairwise from phenyl and cyano, phenacetyl and cyano or benzenesulfonyl and cyano.
Claim 9
Dependent Claim
12 words
The compound of claim 5 wherein each X and Y are cyano.
Claim 10
Independent Claim
82 words
A method for making a compound having the formula: ##STR32##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 benezenesulfonyl and cyano; and M + is one equivalent of an inert cation, which comprises contacting and reacting ##STR33##with CH 2 (LQ) and a strong, non-nucleophilic base in the molar proportion 1:1-2:2-2.5 in an inert solvent, at a temprature of 0° to 30° C.
Claim 11
Independent Claim
82 words
A method for making a compound having the formula: ##STR32##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 benezenesulfonyl and cyano; and M + is one equivalent of an inert cation, which comprises contacting and reacting ##STR33##with CH 2 (LQ) and a strong, non-nucleophilic base in the molar proportion 1:1-2:2-2.5 in an inert solvent, at a temprature of 0° to 30° C.
Claim 12
Dependent Claim
12 words
The method of claim 7 wherein each X and Y is cyano.
References Cited (Backward Citations)
US3366664A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-18 | 1980-07-19 | 1981-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-18 | 1984-07-19 | 1985-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-18 | 1988-07-19 | 1989-01-18 | $7700.00 | Window Closed / Lapsed |