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1,5-Diazabicyclo[4.3.0]non-5-ene is employed for dehydrohalogenation reactions and base-catalyzed rearrangements in organic synthesis. It is an amidine base used in organic synthesis. Further, it is used as a resin curing agent and polyurethane catalyst.
The bicyclic amidines, DBN and DBU are strong organic bases initially introduced as reagents for dehydrohalogenation in vitamin A synthesis: Chem. Ber., 99, 2012 (1966).
For use of DBN in the aldol condensation, see: J. Am. Chem. Soc., 90, 3245 (1968). For esterification of thermally unstable carboxylic acids with diethyl sulfate at ambient temperature, see: Synth. Commun., 6, 89 (1976). For use in the alkylation of thiols with dihalomethanes, see: Synthesis, 952 (1980). In refluxing xylene, DBN and DBU cleave hindered esters, e.g. mesitoates, by alkyl-oxygen cleavage: Tetrahedron Lett., 3987 (1972); J. Org. Chem., 38, 1223 (1973).
Parviainen, A.; Wahlström, R.; Liimatainen, U.; Liitiä, T.; Rovio, S.; Helminen, J. K. J.; Hyväkkö, U.; King, A. W. T.; Suurnäkki, A.; Kilpeläinen, I. Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo[4.3.0]non-5-enium acetate: a batch simulation of the IONCELL-F process. RSC Adv. 2015, 5 (85), 69728-69737.
Barykina-Tassa, O. V.; Snider, B. B. Studies toward the synthesis of cinachyramine. An efficient route to 1,5-diazabicyclo[4.4.0]dec-5-enes. Tetrahedron Lett. 2015, 56 (23), 3151-3154.
Gefahrenhinweise (EU): H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
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