SYMMETRICAL AND UNSYMMETRICAL PYRAZABOLES

• US 3,681,381 A
• Filed: 08/02/1968
• Issued: 08/01/1972
• Est. Priority Date: 08/02/1968
• Status: Expired due to Term

• Current Assignee: Swiatoslaw Trofimenko
• Original Assignee: Swiatoslaw Trofimenko
• Inventors: Trofimenko, Swiatoslaw
• Primary Examiner(s): Mazel, Alex
• Assistant Examiner(s): Dentz, Bernard
• Application Number:
  US04/749,623
• Time in Patent Office: 1,460 Days
• Field of Search: 260/310
• US Class Current: 548/110
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: C07F 5/05 Cyclic compounds having at least one ring containing boron but no carbon in the ring
• CPC Class Codes: C08G 79/08 a linkage containing boron
• CPC Class Codes: C08K 5/55 Boron-containing compounds C08K5/0091 takes precedence

Abstract

Described and claimed are the following: 1. Symmetrical pyrazaboles and sym-triazaboles of the formula

R, R1, R5 and R6 may be hydrogen, halogen, 1-pyrazolyl, alkyl, aryl, alkoxy, haloalkoxy, aryloxy, alkylamino, arylamino, azido, alkylmercapto and arylmercapto; X may be N or CR4; and R2, R3 and R4 may be hydrogen, alkyl, halogen, haloalkyl, aryl, cyano, alkoxy, arylamino, alkoxycarbonyl, nitro, acyl, mercapto and hydroxy with the proviso that R2 and R4 taken together may represent a fused benzo or naphtho structure. In the symmetrical pyrazaboles of this invention either R R1 R5 R6 or R R5 and R1 R6. 2. Unsymmetrical pyrazaboles and sym-triazaboles as represented by formula (I), wherein R and R1 may be hydrogen, halogen, 1-pyrazolyl, alkyl, aryl, alkoxy, haloalkoxy, aryloxy, alkylamino, arylamino, azido, alkylmercapto and arylmercapto; X may be N or CR4; R2, R3 and R4 may be hydrogen, alkyl, halogen, halo-alkyl, aryl, cyano, alkoxy, arylamino, alkoxycarbonyl, nitro, acyl, mercapto and hydroxy with the proviso that R2 and R4 taken together may represent a fused benzo or naphtho structure; and R5 and R6 are defined the same as R and R1 with the proviso that 1-pyrazolyl is excluded as a substituent in the case of R5 and R6. In the unsymmetrical pyrazaboles and sym-triazaboles of this invention, at least one of R and R1 is chemically distinguishable from R5 and R6. 3. The processes by which the pyrazaboles and sym-triazaboles of this invention may be prepared. 4. Polymers having incorporated therein the pyrazabole and symtriazabole structure. The compounds of this invention are useful as polymerization initiators, reducing agents and as reactants in the formation of condensation polymers containing the pyrazabole and symtriazabole moieties.

Claims

1. SYMMETRICAL PYRAZABOLES AND SYM-TRIAZABOLES OF THE FORMULA

2. The compound of claim 1 wherein R2, R3 and R4 are hydrogen;

and R, R1, R5 and R6 are 1-pyrazolyl, 4,4,8,8-tetrakis(1-pyrazolyl)pyrazabole.

3. THE PROCESSES BY WHICH THE PYRAZABOLES AND SYMTRIAZOBLES OF THIS INVENTION MAY BE PREPARED.

4. A compound of claim 1 wherein R2, R3 and R4 are hydrogen;

and R, R1, R5 and R6 are lower alkyl of one to six carbon atoms, 4,4, 8,8-tetraloweralkylpyrazabole.

5. The compound of claim 1 wherein R2, R3 and R4 are hydrogen;

R and R5 are phenyl; and

R1 and R6 are 1-pyrazolyl, 4,8-Diphenyl-4, 8-bis(1-pyrazolyl)pyrazabole.

6. The compound of claim 1 wherein and R, R1, R2, R3, R4, R5 and R6 are hydrogen, pyrazabole.

7. A compound of claim 1 wherein R, R1, R4, R5 and R6 are hydrogen;

and R2 and R3 are lower alkyl of 1 to 6 carbon atoms, 1,3,5,7-tetraloweralkylpyrazabole.

8. The compound of claim 1 wherein R, R1, R4, R5 and R6 are hydrogen and R2 and R3 are phenyl, 1,3,5,7-tetraphenylpyrazabole.

9. A compound of claim 1 wherein R1, R2, R3, R5 and R6 are hydrogen;

and R4 is halogen, 2,6-dihalopyrazabole.

10. The compound of claim 1 wherein R R1 R2 R3 R4 H and R5 R6 fluorine, 4,4-difluoropyrazabole.

11. The compound of claim 1 wherein R R1 R2 R3 R4 H and R5 R6 ethyl, 4,4-diethylpyrazabole.

12. The compound of claim 1 wherein R R1 R2 R3 R4 H and R5 R6 butyl, 4,4,-dibutylpyrazabole.

13. The compound of claim 1 wherein R R1 ethyl, R2 R3 R4 H and R5 R6 chlorine, 4,4-dichloro-8,8-diethylpyrazabole.

14. The compound of claim 1 wherein R and R1 taken together represent o-phenylenedioxy, R2 R3 R4 H and R5 R6 ethyl, 4,4-diethyl-8,8-o-phenylenedioxypyrazabole.

15. The compound of claim 1 wherein R R1 1-pyrazolyl, R2 R3 R4 H and R5 R6 ethyl, 4,4-diethyl-8,8-bis(1-pyrazolyl)pyrazabole.

16. The compound of claim 1 wherein R R1 R4 H, R2 R3 methyl and R5 R6 ethyl, 4,4-diethyl-1,3,5,7-tetramethylpyrazabole.

17. 1,3,5,7-Tetrakis(perfluoroloweralkyl)pyrazabole wherein lower alkyl contains 1-6 carbon atoms.

18. 2,6-Bis(perfluoroloweralkyl)pyrazabole wherein lower alkyl contains one to six carbon atoms.

19. 4,4,8,8-Tetrakis(chloroloweralkoxy)pyrazabole wherein lower alkyl contains one to six carbon atoms.