{ALF} Acetals, including MOM and THP ethers are readily cleaved, as are trityl and TBDMS ethers: Tetrahedron Lett., 25, 2515 (1984). Methyl glycosides are converted to the glycosyl bromides: Tetrahedron Lett., 22, 513 (1981).

{ALD} Beilstein: 4,IV,4008

{ALF} Compare also Iodotrimethyl­silane, A12902.

{ALF} Converts alcohols to alkyl bromides: Tetrahedron Lett., 4483 (1978), and acyl chlorides to acyl bromides: Synthesis, 216 (1981).

{ALF} Effective catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives: Org. Lett., 5, 1661 (2003).

{ALF} Epoxides, oxetanes and THF are cleaved by the reagent: Synthesis, 383 (1981), as are small ring lactones: Angew. Chem. Int. Ed., 18, 689 (1979). The cleavage of acyclic ethers and esters is markedly catalyzed by IBr: J. Org. Chem., 48, 1678 (1983).

{ALF} In combination with DMSO and Et3N, effects the bromolactonization of unsaturated acids: J. Chem. Soc., Perkin 1, 847 (1994).

{SA} J. Chem. Soc., Perkin Trans. II , 263, (1991)

{uni_hamburg} Short: II/14a

{uni_hamburg} Short: II/25C

{ALF} Silylating agent; see Appendix 4. About 104x more reactive than TMSCl in the conversion of ketones to their silyl enol ethers in the presence of Et3N: Liebigs Ann. Chem., 1718 (1980).

{SA} Tetrahedron Lett. 34 , 7713, (1993)