Imidine
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In chemistry imidines are a rare functional group, being the nitrogen analogues of anhydrides and imides. They were first reported by Adolf Pinner in 1883,[1] but did not see significant investigation until the 1950s, when Patrick Linstead and John Arthur Elvidge developed a number of compounds.[2][3]
Imidines may be prepared in a modified Pinner reaction, by passing hydrogen chloride into an alcoholic solution of their corresponding di-nitriles (i.e. succinonitrile, glutaronitrile, adiponitrile) to give imino ethers which then condense when treated with ammonia. As a result, most structures are cyclic.
The compounds are highly moisture sensitive and can be converted into imides upon exposure to water.[2]
See also
References
- ^ Pinner, A. (January 1883). "Ueber die Umwandlung der Nitrile in Imide. Verhalten der Blausäure und des Aethylencyanids gegen Salzsäure und Alkohol". Berichte der Deutschen Chemischen Gesellschaft. 16 (1): 352–363. doi:10.1002/cber.18830160187.
- ^ a b Elvidge, J. A.; Linstead, R. P. (1954). "Heterocyclic imines and amines. Part III. Succinimidine". Journal of the Chemical Society (Resumed): 442. doi:10.1039/JR9540000442.
- ^ Elvidge, J. A.; Linstead, R. P.; Salaman, Ann M. (1959). "37. Heterocyclic imines and amines. Part IX. Glutarimidine and the imidine from α-phenylglutaronitrile". J. Chem. Soc.: 208–215. doi:10.1039/JR9590000208.