Methyl deoxy, carbon-13 nuclear magnetic

As indicated in Section 11,4 (p. 64), direct treatment of alkyl halides with sodium cobalt tetracarbonyl, carbon monoxide, and methanol at elevated temperatures and pressures yields esters. Surprisingly, application of this reaction at 60° (using methanol instead of ether) to methyl tri-0-acetyl-2-deoxy-2-iodo-/3-D-glucopyranoside gave, almost exclusively, the elimination product (88) (in deacetylated form) and a compound presumed to be (on the basis of nuclear magnetic resonance evidence only) the branched-chain ester (87) in less than 0.5 % yield. It is thought that, in the presence of methanol, the sodium cobalt tetracarbonyl dissociates to yield sodium methoxide, and that this causes deacetylation of the substrate. 

---