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1,5-Diazabicyclo(4.3.0)non-5-ene

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) is a chemical compound with the formula CHN. It is an amidine base used in organic synthesis. A related compound with related functions is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The relatively complex nature of the formal names for DBU and DBN (hence the common use of acronyms) reflects the fact that these compounds are bicyclic and contain several functional groups.

Synthesis

DBN could be synthesized in the following manner, similarly to DBU: :[[File:Synthesis-of-DBN.svg|frameless|alt=Synthesis of DBN|600px]]

The synthetic procedure starts with a Michael addition of 2-pyrrolidone to acrylonitrile, followed by hydrogenation, and finally dehydration.

Uses

As a base in organic synthesis

Similar to many other organic bases, DBN could be employed for dehydrohalogenation reactions, base-catalyzed rearrangement reactions, as well as Aldol condensation. Several examples are shown below:

  • Elimination: :[[File:Elimination-by-DBN.svg|frameless|An example of elimination reaction using DBN as the base|450px]]

  • Epimerization of penicillin derivatives, catalyzed by DBN: :[[File:Rearrangement-by-DBN.svg|800px|frameless]]

  • Aldol condensation: :[[File:Aldol-condensation-by-DBN.svg|frameless|An example of aldol condensation|750px]]

DBN salt as an ionic liquid

The acetate salt of DBN is a room-temperature ionic liquid used for processing cellulose fibers by acting as a replacement for the unstable N-Methylmorpholine N-oxide used for making lyocell.

References

References

  1. Savoca, Ann. C. "1,5-Diazabicyclo[4.3.0]non-5-ene" in ''Encyclopedia of Reagents for Organic Synthesis'' (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi. 10.1002/047084289X.rd010.pub2
  2. Möller, F.; Oediger, H. "1,5-Diazabicyclo[5.4.0]undec-5-ene, a New Hydrogen Halide Acceptor" ''Angew. Chem. Int. Ed. Engl. '', '''1967''', ''5'', 76. {{doi. 10.1002/anie.196700761
  3. Oediger, H., Möller, F., & Eiter, K. "Bicyclic Amidines as Reagents in Organic Syntheses" ''Synthesis'', '''1972''', ''11'', 591–598. {{doi. 10.1055/s-1972-21943
  4. Jackson, J.R. and Stoodley, R.J. "Equilibration of penicillanic acid derivatives" ''J. Chem. Soc. D'', '''1971''', 647-648
  5. Corey, E.J., Andersen, N.H., Carlson, R.M. "Total synthesis of prostaglandins. Synthesis of the pure ''dl''-E1, -F1α, -F1β, -A1, and -B1 hormones" ''J. Am. Chem. Soc.'', '''1968''', ''90'', 12, 3245–3247 {{doi. 10.1021/ja01014a053
  6. Zhang, Jinming; Wu, Jin; Yu, Jian; Zhang, Xiaoyu; He, Jiasong; Zhang, Jun. "Application of ionic liquids for dissolving cellulose and fabricating cellulose-based materials: state of the art and future trends." ''Mat. Chem. Front.'' '''2017''', ''1'' (7), 1273-90. {{doi. 10.1039/C6QM00348F
  7. [https://ioncell.fi/ Ioncell - Enter the new era of textile production!]
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amidines non-nucleophilic-bases pyrrolopyrimidines
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