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Ionic liquids can effectively accelerate slow N-benzylation reactions utilizing dibenzyl carbonate as an alkylating reagent. Dibenzyl carbonate (DBzlC) has been used to benzylate phenylacetonitrile, benzyl phenylacetate and phenol. Selective N, N-dibenzylation of primary aliphatic amines was carried with dibenzyl carbonate in the presence of phosphonium salts.
Wen-Chung Shieh,; Mario Lozanov,; Oljan Repič. Accelerated benzylation reaction utilizing dibenzyl carbonate as an alkylating reagent. Tetrahedron Letters. 2003, 44 (36), 6943-6945.
Alessandro Loris,; Alvise Perosa,; Maurizio Selva,; Pietro Tundo. Selective N,N-Dibenzylation of Primary Aliphatic Amines with Dibenzyl Carbonate in the Presence of Phosphonium Salts. J. Org. Chem. 2004, 69 (11) , 3953-3956.
Benzylating agent, e.g. in preparation of benzyl ethers of thiols with K2CO3/ 18-crown-6: Synthesis, 382 (1986). Benzylation of phenols and monobenzylation of active methylene compounds have been accomplished using K2CO3 in DMF: J. Chem. Soc., Perkin 1, 1889 (1995). For N-, O- and S-benzylations in the presence of DBU or DABCO, see: Tetrahedron Lett., 44, 4563 (2003).
Gefahrenhinweise (EU): H302-H312
Harmful if swallowed. Harmful in contact with skin.
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