Claims
- 1. A process for preparing an insecticidal .alpha.-cyano-3-phenoxybenzyl ester of the formula ##STR5## wherein R is selected from 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropyl, 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl, 3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, and 1-(4-chlorophenyl)-2-methylpropyl which comprises reacting an acyl halide of the formula ##STR6## wherein X is chlorine or bromine and R is as defined above with 3-phenoxybenzaldehyde in a mixture of substantially water-immiscible aprotic solvent and an aqueous solution of water-soluble cyanide salt in the presence of a catalytic amount of rate-promoting agent selected from tertiary polyamines which are linear tertiary polyamines of the formula ##STR7## wherein Y is --(CH.sub.2).sub.k -- with k being 1-6, C.sub.3 --C.sub.7 cycloalkane, C.sub.2 --C.sub.6 alkenyl, or C.sub.2 --C.sub.6 alkynyl; z is 1 or 2, and when z is 1, m and n are 0 or independently 1-6, and when m and n are 0, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are hydrocarbon groups, and R.sub.1 may be joined with R.sub.2, and R.sub.3 may be joined with R.sub.4 to form a ring containing the N atom to which both are joined, and when m is 1-6 and n is 0, R.sub.1 and R.sub.3 are absent, and R.sub.2 and R.sub.4 are hydrocarbon groups, and when both m and n are at least 1, R.sub.2 and R.sub.4 are absent; and when z is 2, m and n are 0, R.sub.1 and R.sub.3 are hydrocarbon groups and R.sub.2 and R.sub.4 are absent, 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane, sparteine, and cryptates.
- 2. The process of claim 1 wherein the linear tertiary polyamine is selected from 2,4-dimethyl-2,4-diazapentane, 2,5-dimethyl-2,5-diazahexane, 1,1'-(1,2-ethanediyl)-bis[piperidine], N,N,N',N'-tetramethyl-1,2-diaminocyclohexane, 1,4-dimethyl-1,4-diazacyclohexane, diazabicyclo[2.2.2]octane, 2,6-dimethyl-2,6-diazaheptane, 2,7-dimethyl-2,7-diazaoctane, 2,9-dimethyl-2,9-diazadecane, and 2,5,8,11-tetramethyl-2,5,8,11-tetraazadodecane.
- 3. The process of claim 2 wherein the linear tertiary polyamine is diazabicyclo[2.2.2]octane, 2,6-dimethyl-2,6-diazaheptane, 2,7-dimethyl-2,7-diazaoctane, or 2,5,8,11-tetramethyl-2,5,8,11-tetraazadecane.
- 4. The process of claim 1 wherein the ratepromoting agent is diazabicyclo[2.2.2]octane.
- 5. The process of claim 1 wherein the ratepromoting agent is a cryptate of the formula ##STR8## wherein x and y are independently 1 or 2.
- 6. The process of claim 5 wherein the cryptate is 4,7,13,16,21-pentaoxo-1,10-diazabicyclo[8.8.5]tricosane.
- 7. The process according to any one of claims 1, 2, 3, 4, 5, or 6 wherein R is 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropyl.
- 8. A process according to any one of claims 1, 2, 3, 4, 5, or 6 wherein the water-immiscible aprotic solvent is n-heptane.
- 9. A process according to any one of claims 1, 2, 3, 4, 5, or 6 wherein the water-soluble cyanide salt is sodium cyanide.
Parent Case Info
This is a continuation-in-part of application Ser. No. 079,622, filed Sept. 27, 1979, abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3835176 |
Matsuo et al. |
Sep 1974 |
|
4024163 |
Elliott et al. |
May 1977 |
|
4110363 |
Sheldon |
Aug 1978 |
|
Foreign Referenced Citations (3)
Number |
Date |
Country |
52-142046 |
Nov 1977 |
JPX |
1439615 |
Jun 1976 |
GBX |
2000764 |
Jan 1979 |
GBX |
Non-Patent Literature Citations (2)
Entry |
Normant et al., Synthesis, 805, (1975). |
Vander Zwan et al., J. Org. Chem., vol. 43, 2655, (1978). |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
79622 |
Sep 1979 |
|