Diallyl dicarbonate

Aloe groups are introduced by N-acylation with commercially available allyl chloroformate (bp 109-110 °C) under Schotten-Baumann conditions or diallyl dicarbonate (bp 60 aC/7 Pa) in the presence of base as described above for the introduction of Cbz groups. 

The protection of a-amino groups is usually effected with allyl chloroformate under Schotten-Baumann conditions,P but diallyl dicarbonate (AI0C2O) can also be used.P As with other chloroformates, a severe side reaction is the formation of A -Aloc-protected dipeptides. Since most A -Aloc amino adds are not crystalline compounds, they are preferentially isolated as the corresponding DCHA salts (for A -Aloc amino acids and their analytical characterization, see reff l). 

Allyl esters are synthesized by the azeotropic esterification of amino acids with allyl alcohol in the presence of TosOH or by reaction of N -protected amino acid cesium salts with allyl bromide.P °l They are also available from N -protected amino acids by treatment with allyl alcohol/DCC in or with diallyl dicarbonate in THF with DMAP as cat-... 

We reported the synthesis (data on table 3-3) and some applications of dibenzyl dicarbonate (Ref. 41) and diallyl dicarbonate (Ref. 42). 

Diallyl dicarbonate was used for the allyloxycarbonyl protection of amino compounds including amino acids, amino sugars and nucleosides. Except for the reaction with amino acids, the reagent does not require an additional base, and the only by-products, allyl alcohol and carbon dioxide are both volatile. For example, N-allyloxycarbonyl glucosamine was obtained analytically pure by simple evaporation of the reaction mixture. 

A fourth urethane protecting group, the TV-allyloxycarbonyl group (Alloc) is introduced in the usual way using allyl chloroformate or diallyl dicarbonate. Its main interest concerns its removal by a Pd-catalysed hydrostannolysis with tri-butyltin hydride (Scheme 7.4). It thus provides orthogonal protection without the need to expose the peptide to acid, conditions that would cleave, for example, O-gly-coside derivatives of peptides. 

Diallyl dicarbonate, in D-70111 (2-Oxopropylidene)propanedioic acid Di-Me ester, in 0-70100... 

Di 2-propeny[) ester [115491-93-5]. Diallyl dicarbonate. Diallyl pyrocarbonate CgHjoOs M 186.164... 

In the photoinitiated polymerisation of Jl-vinylpyrrolidinone and N-vinylcaprolactam in dioxane and ethanol, the rate was higher in the latter solvent and monomerlO. This was attributed to the influence of the two additional methylene groups in the caprolactam ring which increases monomer reactivity. Other interesting effects have included the radiation dose on the photopolymerisation of diallyl oxydiethylene dicarbonate O. Here long lived radicals were produced which continue to react in the dark. The rate appears to fit a relaxation model that considers double bonds as traps with increasing lifetimes that are able to transfer to radical sites. 

Diallyl monosulfide. SeeAllyl sulfide Diallyl 2,2 -oxydiethyl dicarbonate. See Diethylene glycol bis (allyl carbonate)... 

Lekishvili N.G., Kandelaki S.A., Asatiani L.P., Tsomaya N.R. / Light-focusing polymer elements based on diallyl esters of meta-carboran dicarbon-acid // BuU.of the Academy of Sciences of Georgia, 1995, vol. 151,Nol,pp. 249-253 [In Georgian],... 

M diallyl 2,2 -oxybis(ethane-2,1-dlyl) dIcarbonate (monomer)... 

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