85336-07-8

Upstream product

• 85335-84-8 erythro-1,4-dichloro-2-bromo-3-(phenylthio)butane 
• 85335-83-7 threo-1,4-dichloro-2-bromo-3-(phenylthio)butane 
• 85335-84-8 (2-Bromo-3-chloro-1-chloromethyl-propylsulfanyl)-benzene 
• 85335-83-7 (2-Bromo-3-chloro-1-chloromethyl-propylsulfanyl)-benzene 
• 28074-23-9 phenylsulfenyl bromide 
• 882-33-7 diphenyldisulfane 
• 85335-86-0 (Z)-1,4-dichloro-2-(phenylthio)-2-butene 
• 85335-85-9 (E)-1,4-dichloro-2-(phenylthio)-2-butene 

Relevant academic research and scientific papers

Studies Related to the Robinson Transposition Reaction

The formation and reactivity of 1,4-dichloro-2-(thio-substituted)-2-butenes is explored, leading to a new bis(phosphonium) salt, 18. 18 may be used as a reagent to effect a functionalized four-carbon annulation sequence, analogous to the well-known Robinson annulation, but yielding enones that are transposed relative to the standard regiochemistry.Some mechanistic studies on the formation of 18 are described, along with trapping studies during the annulation process and various hydrolysis conditions for the resulting dienyl sulfides.Extensive use is made of 13C and 31P NMR and high-field 1H NMR.

The Robinson Transposition Reaction. Conjugate-Addition/Intramolecular Wittig Reactions of Enolates with triphenylphosphonium Chloride

The phosphonium salt described reacts with certain enolates to produce dienyl sulfides that may be subsequently hydrolyzed to afford enones that are regiotransposed relative to the standard Robinson annulation product.