The Reaction between Bis(trimethylsilyl)cyclopentadiene and Dichloroketen, and the Diels-Alder Reactions between N-Phenylmaleimide and Two Silylated Methylcyclopentadienes
Bis(trimethylsilyl)cyclopentadiene reacts with dichloroketen to give only the adduct (7) derived from the 2,5-disilylated isomer (5).Methyl(trimethylsilyl)cyclopentadiene (18) and trimethylsilylmethylcyclopentadiene (21) give Diels-Alder adducts (19) and (20) and (22) and (23) in which the regioselectivity is unaffected by the presence of the silyl group.Epoxidation of the edduct (22) and acid-catalysed opening of the epoxide lead to formation of the exo-methylenenorbornane (26) in a rearrangement controlled by the presence of the silyl group.
Fleming, Ian,Williams, Richard Vaughan
p. 684 - 688
(2007/10/02)
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