synthesis and reactivity of new 1-pentafluorophenyl-1hpyrrole derivatives合成和反应性的新1-pentafluorophenyl-1hpyrrole衍生品.pdf

Molecules 2003, 8, 536-540 molecules ISSN 1420-3049 Synthesis and Reactivity of New 1-Pentafluorophenyl-1H- pyrrole Derivatives KatarÌna Hrnčarikov· and Daniel VÈgh* Department of Organic Chemistry, Slovak University of Technology, RadlinskÈho Street 9, SK-812 37 Tel. (+421) 259325127, Fax. (+421) 252968560 * Author to whom correspondence should be addressed; e-mail: dvegh@chelin.chtf.stuba.sk Received: 13 June 2003 / Accepted: 26 June 2003 / Published 15 July 2003 Abstract: We present 1-pentafluorophenyl-1H-pyrrole and some of its electrophilic substitution reactions: formylation and acetylations. The 2-substituted products formed in these reactions are selectively and in high yield converted into 3-substituted products by treatment with trifluoromethanesulfonic acid. A general synthesis of 3-acylpyrroles was developed by the trifluoromethanesulfonic acidñmediated rearrangement of the corresponding 2-acylpyrroles. Keywords: Conducting materials, supramolecular synthons, pyrroles. Introduction Pyrrole itself and substituted pyrroles are important starting materials for the synthesis of naturally- occuring porphynoid compounds and other porphyrins, potential chemotherapeutic agents and conducting polymers [1]. Polypyrrole films are currently being explored in aplications such as biosensors, adressable gene-ships and interactive conduits for neuronal tissue engineering [2]. Control of molecular architecture of electronic functionalities to the backbone