75238-68-5

Basic information

• Product Name: methyl(4-phenylbut-1-en-1-yl)sulfane
• Synonyms: methyl(4-phenylbut-1-en-1-yl)sulfane
• CAS NO: 75238-68-5
• Molecular Weight: 178.298
• Mol File: 75238-68-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl(4-phenylbut-1-en-1-yl)sulfane(CAS DataBase Reference)
• NIST Chemistry Reference: methyl(4-phenylbut-1-en-1-yl)sulfane(75238-68-5)
• EPA Substance Registry System: methyl(4-phenylbut-1-en-1-yl)sulfane(75238-68-5)

Safety Data

• Hazardous Substances Data: 75238-68-5(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 1779-54-0 methylthiomethyl(triphenyl)phosphonium chloride 
• 925-89-3 Prop-1-en-1-thiol 
• 100-44-7 benzyl chloride 
• 74-88-4 methyl iodide 
• 100-39-0 benzyl bromide 
• 10152-76-8 allylmethyl sulfide 
• 6937-97-9 allyl(benzyl)sulfide 

Downstream Products

• 1345987-84-9 C₂₁H₂₅N 
• 1345987-85-0 C₂₄H₂₉NO₂ 

Relevant articles and documents

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

Phosphines were previously unusable as Pummerer-type nucleophiles due to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient and versatile two-step one-carbon homologation of aldehydes to ketones.

REARRANGEMENTS OF THE CARBANIONS DERIVED FROM ALLYL BENZYL THIOETHER

The metalation of allyl benzyl thioether involves the benzylic or the allylic hydrogens.The benzylic carbanion undergoes a rapid sigmatropic shift whereas the allylic carbanion gives rise to various rearrangements, among them migration of the allylic unit to the para position with allylic inversion.The temperature dependence of the ratio of products arising from the benzylic carbanion vs those from the allylic carbanion shows that the allylic-to-benzylic carbanion transformation occurs only under special conditions: (a) with slow addition of the base; (b) with thioether in excess relative to the base, and (c) on raising the temperature of the reaction medium from -78 deg C to -15 deg C.In the last instance, the proton transfer is intramolecular as shown with labeled thioethers.The extent of the different rearrangements depends on the temperature and solvent.A choise of mechanism cannot be made at this time for the para migration 5-->9a.A leaving group effect on the reaction regioselectivity of the carbanion from allyl methyl thioether with benzyl halides has been noticed.The presence of dibenzyl indicates that, in addition to SN2 reactions, some electron transfer process is occuring.