93903-57-2

Basic information

• Product Name: (E)-5-phenylpent-4-en-1-yl 4-methylbenzenesulfonate
• CAS NO: 93903-57-2
• Molecular Weight: 316.421
• Mol File: 93903-57-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-5-phenylpent-4-en-1-yl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-5-phenylpent-4-en-1-yl 4-methylbenzenesulfonate(93903-57-2)
• EPA Substance Registry System: (E)-5-phenylpent-4-en-1-yl 4-methylbenzenesulfonate(93903-57-2)

Safety Data

• Hazardous Substances Data: 93903-57-2(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 100-42-5 styrene 
• 19300-54-0 toluene-4-sulfonic acid pent-4-enyl ester 
• 28525-69-1 (4E)-5-phenyl-4-pentenoic acid 
• 13159-16-5 (E)-5-phenyl-4-penten-1-ol 

Downstream Products

• 13159-19-8 diethyl (E)-2-(5-phenylpent-4-enyl)malonate 
• 16765-45-0 erythro-phenyl(tetrahydrofuran-2-yl)methanol 
• 1246366-02-8 (E)-N-(4-nitrobenzenesulfonyl)-5-phenylpent-4-enylamine 
• 189322-54-1 (E)-pent-1-ene-1,3-diyldibenzene 
• 97455-11-3 (E)-β-(3-phenyl-1-propyl)styrene 
• 16424-56-9 trans 6-phenyl-5-hexenoic acid 
• 148470-51-3 (E)-5-(benzylthio)-1-phenyl-1-pentene 
• 910788-16-8 (E)-(5-iodopent-1-en-1-yl)benzene 
• 16424-52-5 (E)-6-Phenylhex-5-enenitrile 

Relevant articles and documents

Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles

The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated SN2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.

Regiochemical and Stereochemical Studies on Halocyclization Reactions of Unsaturated Sulfides

The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent.Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts.The endo- versus exo-regioselectivity of these alkenyl sulfide ring closure most likely reflects the difference in thermodynamic stabilities of the β-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate.The efficiency of cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers.Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides.Conversely, the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length.Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring.The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control.The methodology has been applied to the synthesis of unusual bicyclic β-lactams related to the penicillin family of antibiotics.