Propargyl alcohol - Product Finder - Products BASF
The difluorovinyl propargyl ether 11 produced by reduction of 2-bromodifluoromethyl substituted propargyl vinyl ether 3b rearranged in hot benzene to give the corresponding allene 12 bearing a gem -difluoromethylene group in the middle of the aliphatic chain.
and I found one that reacted propargyl alcohol to methacryloyl ..
N2 - A method is described for the oxidative Meyer-Schuster-type rearrangement of propargylic alcohols to (Z)-α-chloro- and α-iodoenones using VOCl3 as a multifunctional reagent. The vanadium reagent is found to serve as rearrangement promoter as well as an active chlorenium ion donor. Yields are improved when VOCl3 is employed in conjunction with N-halosuccinimide reagents, giving some insights into the complex mechanism.
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Synthesis of Propargyl-Terminated Heterobifunctional …
The reaction of ethyl α-per(poly)fluoroalkyl acetate 1 with 1-phenyl propargyl alcohol 5 in refluxing CH 2 Cl 2 in the presence of the mixed base (Na 2 CO 3 /TEA) directly afforded the corresponding unsaturated fluoroalkyl ketone 6a - c in one pot.
Synthesis of Propargyl-Terminated Heterobifunctional ..
In order to test conditions that might effect the key transformation, we needed a model system for which the substrate and product would be non-volatile and easily handled. Furthermore, we desired a model substrate that could be prepared easily from commercially available materials by a short sequence. We believed that the substrate requirements would be met by propargyl alcohol 9 (), which we considered the addition product of alkyne 7 and cyclohexanecarboxaldehyde (8). Iodoolefinic alkyne 7 might be conveniently prepared from the inexpensive 10-undecenal (4). Therefore, we converted aldehyde 4 to the iodo olefin 5 and then cleaved the unsubstituted terminal double bond with OsO4 followed by NaIO4 to obtain aldehyde 6. Treatment of this compound with the Ohira-Bestmann reagent afforded alkyne 7. Addition of the corresponding Carreira reagent to aldehyde 8 afforded substrate 9 for our feasibility studies.
Allyl alcohol; Propargyl; Propargyl chloride; References Edit
The particular system of interest to us was the conversion of propargyl alcohol 3 to cis allylic alcohol 2, an advanced intermediate in a projected short synthesis of discodermolide 1 (). Olefin 2 would need only a protection step before linkage to a stereopentad-containing synthon, a key step that would complete the construction of the carbon skeleton of the target. The ability of the vinyl iodide to withstand the reduction conditions was essential to the optimal convergence of the synthesis.
Synthesis of C-Propargylic Esters of N-Protected …
Our interest in designing and implementing optimally convergent schemes for the synthesis of polyketide antibiotics led us to consider the possibility of directly reducing the alkyne bond of a propargyl alcohol system to a cis olefin in the presence of a vinyl iodide. Vinyl iodides are generally believed to be incompatible with conditions that would reduce an alkyne to an olefin or to a saturated carbon-carbon bond.