A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Org. Synth. 1952, 32, 48
DOI: 10.15227/orgsyn.032.0048
Submitted by C. G. Overberger and M. B. Berenbaum1.
Checked by N. J. Leonard and E. H. Mottus.
1. Procedure
In a 200-ml. flask equipped with a reflux condenser are placed 20 g. (0.082 mole) of 1,1'-azo-bis-1-cyclohexanenitrile (p. 66) and 50 ml. of toluene. The solution is heated under gentle reflux for 8 hours, and the reaction mixture is placed in a refrigerator overnight. The product is collected on a Büchner funnel and air-dried; yield 11.5–12.2 g. (65–69%); m.p. 224.5–225.5° (Note 1).
2. Notes
1. Tetramethylsuccinonitrile can be prepared from 2,2'-azo-bis-isobutyronitrile in a similar manner.2 In this case petroleum ether (b.p. 60–70°) is added to the reaction mixture before cooling it overnight. The yield is 75–81% of the theoretical amount; m.p. 168–170°. Sublimation at 20–50 mm. raises the melting point to 170.5–171.5° with very little loss of material.
3. Discussion
1,1'-Dicyano-1,1'-bicyclohexyl has been prepared previously by Hartman3 in a similar manner. The procedure has been substantiated by Overberger, O'Shaughnessy, and Shalit.4

References and Notes
  1. Polytechnic Institute of Brooklyn, Brooklyn, New York.
  2. Thiele and Heuser, Ann., 290, 1 (1896).
  3. Hartman, Rec. trav. chim., 46, 150 (1927).
  4. Overberger, O'Shaughnessy, and Shalit, J. Am. Chem. Soc., 71, 2661 (1949).

Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)

petroleum ether

toluene (108-88-3)

Tetramethylsuccinonitrile (3333-52-6)


1,1'-AZO-bis-1-CYCLOHEXANENITRILE (2094-98-6)

[Bicyclohexyl]-1,1'-dicarbonitrile (18341-40-7)