133360-01-7Relevant articles and documents
THE FLUORINATION OF SIMPLE FIVE-MEMBERED HETEROAROMATIC COMPOUNDS WITH ELEMENTAL FLUORINE
Cerichelli, Giorgio,Crestoni, Maria Elisa,Fornarini, Simonetta
, p. 749 - 755 (2007/10/02)
The reaction of elemental fluorine with five-membered heteroaromatics under controlled conditions proceeds cleanly, yielding major substitution products in the case of thiophene (1) and N-methylpyrrole (2) or 1,4-addition products in the case of furan (3), while pyrrole (4) gives only tars.The site of fluorine substitution on N-methylpyrrole remarkably favours the β carbon atoms by a factor of ca. 3 over the α carbons.The α/β substitution ratio for 1 (1.9) and 2 (0.28) and the intermolecular reactivity order N-methylpyrrole > thiophene > benzene agrees with a polar electrophilic substitution mechanism.Also the predominantly syn 1,4-addition to furan conforms to the polar syn addition of F2 to double bonds.