119950-30-0

Upstream product

• 119950-22-0 2-bromo-1,1,3-tris(phenylthio)propane 
• 105961-98-6 (E)-1,3,3-tris(phenylthio)propene 
• 75-77-4 chloro-trimethyl-silane 
• 102070-37-1 1,1-bis(phenylthio)-3-phenylthio-1-propene 
• 108-98-5 thiophenol 

Relevant academic research and scientific papers

γ-SUBSTITUTED KETENE THIOACETALS AS β-LITHIOACRYLATE EQUIVALENTS. THE SYNTHESIS OF (+/-)-ELDANOLIDE

Lithiation of 1,1-bis(phenylthio)-3-phenylthio-1-propene 3 and reaction with a range of electrophiles gave exclusively the γ-substituted product 4.This reagent has been used in a short synthesis of the pheromone, (+/-)-eldanolide.

Synthesis and Reactivity of Lithiated γ-Functionalised Ketene Dithioacetals. Generation of a Flexible β-Lithioacrylate Equivalent

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.