1,5-Diazacyclooctane Explained

1,5-Diazacyclooctane is an organic compound with the formula (CHCHCHNH). It is a colorless oil. 1,5-Diazacyclooctane is a cyclic diamine.^[1]

Synthesis and reactions

It is prepared in low yield by the alkylation of ammonia with 1,3-dibromopropane.^[2]

The N-H centers can be replaced with many other groups. As a bis secondary amine, it condenses with aldehydes to give bicyclic derivatives.^[3] When treated with transition metal salts, it serves as a chelating ligand.^[1]

Related compounds

• 1,4-Diazacycloheptane
• 1,5-Diaza-3,7-diphosphacyclooctanes
• Tröger's base

Notes and References

1. Coordination Chemistry of Bidentate Medium Ring Ligands (Mesocycles) . Musker, W. Kenneth. Coordination Chemistry Reviews . 1992. 117. 133–57. 10.1016/0010-8545(92)80022-J.
2. Book: Inorganic Syntheses. Daniel K. Mills . Ivan Font . Patrick J. Farmer . Yui-May Hsiao . Thawatchai Tuntulani . Rizalia M. Buonomo . Dawn C. Goodman . Ghezai Musie . Craig A. Grapperhaus . Michael J. Maguire . Chia-Huei Lai . Michelle L. Hatley . Jason J. Smee . John A. Bellefeuille . Marcetta Y. Darensbourg . 1,5-Diazacyclooctane, Pendant Arm Thiolato Derivatives and [ N,N′ -Bis(2-Mercaptoethyl)-1,5-Diazacyclooctanato]Nickel(II) . 3 . 1998. 32. 89–98. 10.1002/9780470132630.ch15. 9780471249214 .
3. Reaction of 1,5-Diazacyclooctane with Aldehydes. Billman, John H. . Dorman, Linneaus C.. Journal of Organic Chemistry. 1962. 27. 7 . 2419–22. 10.1021/jo01054a033.