167777-15-3Relevant academic research and scientific papers
Allylation of sugar diols under phase transfer conditions using potassium carbonate as a base. Unexpected formation of cyclic carbonates
Jarosz,Szewczyk
, p. 1115 - 1122 (2007/10/03)
Allylation of sugar vic-diols (with a primary and secondary OH groups) under the phase transfer conditions (allyl bromide, K2CO3, 18-crown-6, toluene) afforded a mixture of both monosubstituted allyl ethers and small amounts of the di-allyl derivative. Interestingly, the cyclic carbonate was also isolated from the post reaction mixture. Its formation may be explained by reaction of the di-allyl carbonate, formed in situ under the reaction conditions, with the 1,2-diol. The structure of mono-allylated isomers can be easily assigned from the chemical shift (δc) of the CH2OR group (for R = H; All).
