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1-(Triisopropylsilyl)pyrrole may be employed as reagent in perfluoroalkylation and Vilsmeier formylation reactions. It may be used in the preparation of ethyl 2-(2,4-dinitrophenylhydrazono]-3-[ 1-(triisopropylsily1)-pyrrol-2-yflpropanoate; heterocyclic base, 3-nitropyrrole and 3-nitropyrrole, required for the synthesis of 1 -(2?-deoxy-β-D-ribofuranosyl)-3-nitropyrrole. It participates in various electrophilic substitution reactions specifically at β-position, via reaction with various electrophilic reagents (Br+, I+,NO2+,etc).
Cristiano Zonta; Fabrizio Fabris; Ottorino De Lucchi. The pyrrole approach toward the synthesis of fully functionalized cup-shaped molecules. Org. Lett. 2005, 7,(6), 1003-1006.
Izzat T.Raheem; Parvinder S.Thiara; Eric N.Jacobsen . Regio- and enantioselective catalytic cyclization of pyrroles onto N-acyliminium ions. Org. Lett. 2008, 10,(8), 1577-1580.
Valuable intermediate in which the bulky TIPS group promotes regioselective 3-substitution. Bromination, nitration and base-catalyzed acylation all occur regioselectively at the 3-position: Tetrahedron Lett., 24, 3455 (1983). Metallating agents also attack at the 3-position: J. Org. Chem ., 55, 6317 (1990); 57, 1653 (1992). The silyl group is easily removed with F -, e.g. TBAF. For a review of synthesis of 3-substituted pyrroles, see: Synthesis, 353 (1985). Compare 1-(Phenylsulfonyl)pyrrole, A11599.
Hazard Statements: H302
Harmful if swallowed.
Precautionary Statements: P280f
Wear protective clothing.