131365-16-7Relevant academic research and scientific papers
Synthesis and Reactivity of Lithiated γ-Functionalised Ketene Dithioacetals. Generation of a Flexible β-Lithioacrylate Equivalent
Dziadulewicz, Edward,Hodgson, David,Gallagher, Timothy
, p. 3367 - 3374 (2007/10/02)
The synthesis of 1,1,3-tris(phenylthio)prop-1-ene (8) is described.Anion (9), obtained by deprotonation of (8) with lithium di-isopropylamide, reacts with a wide range of electrophiles to give the γ-substituted adducts (10) exclusively.The relative importance of steric and electronic effects in determining the high γ-regioselectivity observed for (9) have been evaluated using a series of related ketene dithioacetals (12)-(15), and (17).The equivalence of anion (9) to a β-lithioacrylate has been illustrated by constructing a series of α,β-unsaturated γ- and δ-lactones and a short synthesis of (+/-)-eldanolide is also described.Anion (9) undergoes a facile dimerisation in the presence of oxygen to give dimer (20) and a mechanistic rationale for this observation is presented.
