Org. Synth. 1952, 32, 48
DOI: 10.15227/orgsyn.032.0048
1,1'-DICYANO-1,1'-BICYCLOHEXYL
[[Bicyclohexyl]-1,1'-dicarbonitrile]
Submitted by C. G. Overberger and M. B. Berenbaum
1.
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 Hartman
3 in a similar manner. The procedure has been substantiated by Overberger, O'Shaughnessy, and Shalit.
4
Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
petroleum ether
toluene (108-88-3)
Tetramethylsuccinonitrile (3333-52-6)
2,2'-Azo-bis-isobutyronitrile
1,1'-AZO-bis-1-CYCLOHEXANENITRILE (2094-98-6)
1,1'-DICYANO-1,1'-BICYCLOHEXYL,
[Bicyclohexyl]-1,1'-dicarbonitrile (18341-40-7)
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