103902-77-8Relevant academic research and scientific papers
ALKENYLIRON COMPLEXES. CYCLOADDITION REACTIONS OF ORGANOIRON METALLOALKADIENES
Waterman, Paul S.,Belmonte, John E.,Bauch, Thomas E.,Belmonte, Patricia A.,Giering, Warren P.
, p. 235 - 250 (1985)
The metalloalkadienes, 2-Fp-1,3-butadiene (5), 1-Fp-1,3-butadiene (6), and 1-Fp-3-methyl-1,3-butadiene (7) (Fp = η-C5H5(CO)2Fe) form Diels-Alder adducts with a variety of electrophilic dienophiles.Kinetic experiments have demostrated that 5 is at least 100 times more reactive toward dimethyl acetylene dicarboxylate than 2-trimethylsiloxy-1,3-butadiene. 5 and toluene sulfonyl isocyanate from an imino lactone that is thought to arise via a stepwise process involving ionic species.The synthetic utility of 5 is limited by its low decomposition point (110 deg C) and the formation of nearly equimolar quantities of the 1,3- and 1,4-positional isomers of cycloadducts derived from several asymmetric dienophiles.
