120263-38-9Relevant academic research and scientific papers
1-Formyl- and 1-Diazoalkanesulfonates
Berkessel, Albrecht,Voges, Markus
, p. 1147 - 1152 (2007/10/02)
The deprotonation of the neopentyl, isobutyl and isopropyl esters of methane- and ethanesulfonic acid with n-butyllithium and subsequent reaction with ethyl formate afforded the corresponding 1-formylalkanesulfonates in 77-90percent yield. 1-(Methoxymethylene)alkanesulfonates could be obtained by additional treatment with dimethyl sulfate and base, as examplified in the case of neopentyl 1-formylethanesulfonate.Furthermore, the formylated sulfonates were converted into the stable 1-diazoalkanesulfonates in 28-65percent yield employing arylsulfonyl azides as diazo group transfer reagents.The chemical behaviour of the novel 1-diazoalkanesulfonates resembles that of 1-diazoalkanephosphonates, e.g., deprotection to the 1-diazoalkanesulfonate anion resulted in rapid denitrogenation.The thermolysis of isobutyl 1-diazoethanesulfonate in an inert solvent afforded isobutyl vinylsulfonate as the major product. - Keywords: 1-Formylalkanesulfonates; 1-Diazoalkanesulfonates
