82262-89-3Relevant academic research and scientific papers
SILICON IN ORGANIC SYNTHESIS. 12. trans-1-BENZENESULFONYL-2-(TRIMETHYLSILYL)ETHYLENE, A DIELS-ALDER DIENOPHILE EQUIVALENT OF ACETYLENE AND MONOSUBSTITUTED ACETYLENES
Paquette, Leo A.,Williams, Richard V.
, p. 4643 - 4646 (1981)
trans-1-Benzenesulfonyl-2-(trimethylsilyl)ethylene and its 1,2-d2 derivative enter into Diels-Alder cycloaddition to give products which are smoothly eliminated with fluoride ion.Alkylation of the α-sulfonyl carbanion can precede elimination, s
Dienophilic Properties of Phenyl Vinyl Sulfone and trans-1-(Phenylsulfonyl)-2-(trimethylsilyl)ethylene. Their Utilization as Synthons for Ethylene, 1-Alkenes, Acetylene, and Monosubstituted Alkynes in the Construction of Functionalized Six-Membered Rings via ? Cycloaddition Meth.
Carr, Richard V. C.,Williams, Richard V.,Paquette, Leo A.
, p. 4976 - 4986 (2007/10/02)
Useful procedures for effecting the indirect capture of ethylene, acetylene, 1-alkenes, and monosubstituted alkynes in Diels-Alder cycloadditions have been developed.In the first sequence, phenyl vinyl sulfone is shown to enter into ? reactions as a moderately reactive dienophile and to do so with very good regioselectivity.The resulting adducts can be directly desulfonated or alkylated prior to such reduction.A wide range of functional groups can be appended in this fashion at a specific locus within the newly formed six-membered ring.When the analogous chemistry is applied to trans-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene (2), adducts result which undergo ready fluoride ion induced elimination with efficient introduction of a double bond.The use of 2 and its d2 derivative is highlighted by the synthesis of several functionalized dibenzobarrelenes.
