182194-89-4

Basic information

• Product Name: Toluene-4-sulfonic acid (E)-1-methyl-5-phenyl-pent-4-enyl ester
• Synonyms: Toluene-4-sulfonic acid (E)-1-methyl-5-phenyl-pent-4-enyl ester
• CAS NO: 182194-89-4
• Molecular Weight: 330.448
• Mol File: 182194-89-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Toluene-4-sulfonic acid (E)-1-methyl-5-phenyl-pent-4-enyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Toluene-4-sulfonic acid (E)-1-methyl-5-phenyl-pent-4-enyl ester(182194-89-4)
• EPA Substance Registry System: Toluene-4-sulfonic acid (E)-1-methyl-5-phenyl-pent-4-enyl ester(182194-89-4)

Safety Data

• Hazardous Substances Data: 182194-89-4(Hazardous Substances Data)

Upstream product

• 102-92-1 cinnamoyl chloride 
• 69371-59-1 6-phenyl-hex-5-en-2-one 
• 58927-89-2 (+/-)-(E)-6-phenylhex-5-en-2-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant articles and documents

Photoreactions of Phenyl-Substituted N-(Pent-4-enyl-1-oxy)pyridine-1(1H)-thiones

A series of hitherto unknown N-(pent-4-enyl-1-oxy)pyridine-2(1H)-thiones (6) were prepared from substituted pent-4-enyl tosylates or benzylic chlorides.On irradiation with incandescent light heterocycles 6 liberated alkoxy radicals 2, which were studied for rearrangement reactions.Surprisingly, all transformations involving the 1-phenylpent-4-enyl-1-oxy radical (2a), for example, to give the substituted thioether 8, 2-bromomethyl-5-phenyltetrahydrofuran (11), or the tetrahydrofuran 14a, were not stereoselective.On the other hand 2-, 3-mono-, and 1,5-disubstituted pent-4-enyl-1-oxy radicals 2d-e and 2g cyclized in good yields and with good to excellent stereoselectivities to give the corresponding 2,4-cis- and 2,3-trans-phenyltetrahydrofurfuryl radicals 3d-e, and the trans-2-benzyl-5-methyl substituted intermediate 3g.The major reaction mode of the 4-phenylpent-4-enyl-1-oxy radical (2f) was the 6-endo cyclization, which afforded 3-phenyltetrahydropyran (13f) as the major product (endo:exo=93:7) after trapping with hydrogen donors.According to the experimental data of the present study, the unusual reactivity of the 1-phenylpent-4-enyl-1-oxy radical (2a) in 5-exo-trig ring closures could be caused by a coplanar arrangement of the benzyloxy moiety in the transition state of the cyclization.This interaction would lock the radical center in 2a in a preferred conformation, which would result in similar steric effects for both cis- and trans-cyclizations. - Keywords: alkoxy radicals; cyclizations; pyridinethiones; radicals; tetrahydrofurans