1990
DOI: 10.1080/00397919008052307
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Hydroxyalkylation of Diethylvinylphosphonate in the Presence of DABCO

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Cited by 24 publications
(7 citation statements)
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“…A novel method for the generation of functionalized polymers that has largely been under-explored is the use of monomers derived from the Baylis–Hillman reaction. The Baylis–Hillman reaction is a carbon–carbon bond forming reaction between an aldehyde and an activated alkene in presence of a tertiary amine such as DABCO (1,4-diazabicyclo[2.2.2]octane), and provides densely functionalized molecules in a one-pot process (Figure ). Several activated alkenes such as acrylates, acrylamides, acrylonitriles, vinyl ketones or vinyl phosphonates are substrates for the Baylis–Hillman reaction.…”
Section: Introductionmentioning
confidence: 99%
“…A novel method for the generation of functionalized polymers that has largely been under-explored is the use of monomers derived from the Baylis–Hillman reaction. The Baylis–Hillman reaction is a carbon–carbon bond forming reaction between an aldehyde and an activated alkene in presence of a tertiary amine such as DABCO (1,4-diazabicyclo[2.2.2]octane), and provides densely functionalized molecules in a one-pot process (Figure ). Several activated alkenes such as acrylates, acrylamides, acrylonitriles, vinyl ketones or vinyl phosphonates are substrates for the Baylis–Hillman reaction.…”
Section: Introductionmentioning
confidence: 99%
“…The conversion of 1 to 4 is equivalent to the Baylis−Hillman reaction. , We describe herein that treatment of a mixture of 1 and carbonyl compounds with LDA afforded 4 in good to high yields. Furthermore, we provide mechanistic evidence for the intermediacy of 2 .…”
mentioning
confidence: 96%
“…The main products of the reaction at 413 K were keto alcohol 29 (44%) and diol 28 (30%); a-hydroxy aldehyde 30 was also identified with 2% yield (Scheme 6) [32]. The product distribution was similar to that obtained in the presence of montmorillonite clay [34] and differed sufficiently from that in the presence of ZnBr 2 [35].…”
Section: Thermolysis Of Verbenol Verbenol Epoxide and Verbenone Epoxidementioning
confidence: 80%