G. Brooke
Apr 13, 1982
Citations
0
Influential Citations
10
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
Pentafluorophenyl and heptafluoro-2-naphthyl prop-2-ynyl ethers [(1) and (5)] react in N,N-diethylaniline to give among other products 2-methylfuran derivatives [(10) and (11); (15)] formed by hydrogen-abstraction reactions, and 2-(diethylaminobenzyl)furan derivatives [(13) and (14); (17) and (18)]; the 2-fluoromethylfuran (16) is also formed from (5). No aromatic substitution products are obtained from (5) with nitrobenzene or benzylidyne trifluoride. It was not possible to distinguish between homolytic and heterolytic fission of the aliphatic C–F bonds in the Claisen rearrangement intermediates (8) and (9) involved in these reactions.