For use in dehydrohalogenation, see, e.g. Org. Synth. Coll., 9, 247, 663 (1998). Reportedly superior to imidazole for the preparation of TBDMS derivatives of, e.g. amines, thiols and carboxylic acids: Tetrahedron Lett., 26, 475 (1985). Promotes the epoxidation of ɑ?-unsaturated δ-lactones and other enones by t-butyl hydroperoxide, where other bases fail: Tetrahedron, 51, 8573 (1995). Used in the Wittig reaction to generate ylides stabilized by aryl or electron-withdrawing groups, see: Chem. Ber., 99, 2012 (1966). DBU forms hydrogen-bonded complexes with carboxylic acids, which can be alkylated in good yield by alkyl bromides or iodides, in a simple esterification procedure: Bull. Chem. Soc. Jpn., 51, 2401 (1978). In combination with NBS in MeOH, promotes the Hofmann rearrangement of amides to give methyl carbamates under mild conditions: J. Org. Chem., 62, 7495 (1997). For a review of the chemistry of DBU and other pyrimidoazepines, see: Adv. Heterocycl. Chem., 42, 84 (1987).
