# US 4,399,076 A · 1,1-Disubstituted 2-vinyl- and 2-ethylcyclopropanes

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- Number: US 4,399,076 A
- Document ID: US4399076A
- Status: Granted
- Kind: A
- Application number: 06/350,669
- Filed: 1982-02-22
- Granted: 1983-08-16
- Earliest claimed: 1982-02-22
- Assignees: National Distillers and Chemical Corporation
- Inventors: Richard G. Fayter, Jr.; Allen L. Hall
- Web page: https://patentgrep.com/patent/US4399076A

## CPC

- C07C 255/00: Carboxylic acid nitriles (cyanogen or compounds thereof C01C3/00)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

2-Vinyl- and 2-ethylcyclopropanes having an aryl group and a nitrogen-containing radical substituted at the 1-position on the ring are provided. The novel 1,1-disubstituted 2-vinylcyclopropane and 2-ethylcyclopropane compounds of this invention have utility in herbicidal applications and are useful reactants. The 2-vinylcyclopropane derivatives are useful monomers for anionic and radical polymerizations.

## Claims

### Claim 1

A compound of the formula ##STR23## where R is an ethyl or vinyl group, R' and R" are hydrogen, halogen, nitro or a hydrocarbon radical having from 1 to 20 carbon atoms and Y is
(a) nitrile;
(b) an amine of the formula ##STR24## where y is an integer from 0 to 6 and R.sub.1 and R.sub.2 are hydrogen, alkyl, hydroxyalkyl, aryl, carboalkoxy or carbamyl; or
(c) a quaternary amine of the formula ##STR25## where y is an integer from 0 to 6, R.sub.3, R.sub.4 and R.sub.5 are alkyl, aryl, or hydroxyalkyl and X is halide, hydroxide, sulfate, nitrate, alkylsulfate, alkylphosphate or fluoroborate.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R' and R" are hydrogen, chloro, bromo, fluoro, nitro or an alkyl, aryl, cycloalkyl, alkoxyl or hydroxyalkyl group having from 1 to 12 carbon atoms.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein R.sub.1 and R.sub.2 are C.sub.1-8 alkyl, C.sub.1-8 hydroxyalkyl, C.sub.6-12 aryl, carboalkoxy of the formula ##STR26## where R* is C.sub.1-8 alkyl, or carbamyl of the formula ##STR27## where R** is hydrogen, C.sub.1-8 alkyl, C.sub.1-8 aryl, alkaryl or aralkyl, and R.sub.3, R.sub.4 and R.sub.5 are C.sub.1-8 alkyl, C.sub.1-8 hydroxyalkyl or C.sub.6-12 aryl.

### Claim 4

A compound of the formula ##STR28## where R is ethyl or vinyl and R'" is hydrogen, chloro, bromo, fluoro, nitro, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxyl.

### Claim 5

A compound of the formula ##STR29## where R is ethyl or vinyl, R'" is hydrogen, chloro, bromo, fluoro, nitro, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxyl, and R.sub.6 is hydrogen or C.sub.1-8 alkyl.

### Claim 6

A compound of the formula ##STR30## where R is ethyl or vinyl, R'" is hydrogen, chloro, bromo, fluoro, nitro, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxyl, R.sub.7 is C.sub.1-8 alkyl, and X is halide, hydroxide, sulfate, nitrate, alkylsulfate, alkylphosphate or fluoroborate.

### Claim 7

A compound of the formula ##STR31## where R is ethyl or vinyl and R'" is hydrogen, chloro, bromo, fluoro, nitro, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxyl.

### Claim 8

A compound of the formula ##STR32## where R is ethyl or vinyl, R'" is hydrogen, chloro, bromo, fluoro, nitro, C.sub.1-4 alkyl, C.sub.1-4 hydroxyalkyl or C.sub.1-4 alkoxyl, and R.sub.7 is a C.sub.1-8 alkyl.