35346-80-6Relevant academic research and scientific papers
Synthese de sulfures et dithioacetals alleniques et leurs transformations en composes carbonyles α,β-insatures
Guittet, Eric,Bibang Bi Ekogha, Cyriaque,Julia, Sylvestre A.
, p. 325 - 331 (2007/10/02)
The nucleophilic addition of various organo-lithium compounds to 1-methylthio- (or 1-phenylthio)-3-methyl-3-buten-1-yne 3 in ether affords α-lithiated allenic sulfides 4 which on protonation give 1-methylthio-3-methyl-1,2-alkadienes.These allenic sulfides can be hydrolysed into the corresponding α,β-unsaturated aldehydes by use of cupric salts in aqueous acetone.Treatment of the lithio-derivative 4aa with methyl iodide, followed by mercuric chloride in aqueous acetonitrile, yields the α,β-unsaturated methyl ketone 14 (R2=n.C4H9; R=CH3).Treatment of the lithio-derivatives 4 with methyl disulfide affords allenic dithio-acetals, which are readily hydrolysed into the corresponding methyl α,β-unsaturated esters by use of cupric salts in methanol.
