105235-55-0

Basic information

• Product Name: Benzene, 1-(2-hexenylsulfonyl)-4-methyl-, (E)-
• CAS NO: 105235-55-0
• Molecular Formula: C13H18O2S
• Molecular Weight: 238.351
• Mol File: 105235-55-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(2-hexenylsulfonyl)-4-methyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(2-hexenylsulfonyl)-4-methyl-, (E)-(105235-55-0)
• EPA Substance Registry System: Benzene, 1-(2-hexenylsulfonyl)-4-methyl-, (E)-(105235-55-0)

Safety Data

• Hazardous Substances Data: 105235-55-0(Hazardous Substances Data)

Upstream product

• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 2305-21-7 2-hexen-1-ol 
• 99704-81-1 trans-2-hexenyl mesylate 
• 10486-08-5 sodium p-thiocresolate 
• 4798-44-1 1-hexene-3-ol 
• 928-95-0 (E)-2-Hexen-1-ol 
• 106709-73-3 (E)-2-hexenyl p-toluenesulfinate 
• 119365-11-6 (Z)-hexenyl p-toluenesulfinate 
• 119306-19-3 (E)-2-hexenyl p-tolyl sulfide 
• 119306-00-2 1-hexen-3-yl p-toluenesulfinate 
• 71964-05-1 1-tosyl-1-hexene 

Relevant articles and documents

Water-Promoted Dehydrative Tsuji–Trost Reaction of Non-Derivatized Allylic Alcohols with Sulfinic Acids

A mild, green and extra activator-free synthesis of allylic sulfones from non-derivatized allylic alcohols and sulfinic acids was developed and only the easily-available Pd(PPh3)4 was used as the catalyst. This new method could be easily scaled up to gram scale, affording the target allylic sulfones in a nearly quantitative yield with water as the sole by-product. Mechanism studies both by various NMR techniques and by theoretical calculations suggested two reaction pathways may be involved in the reaction, which are dependent on the reaction media, that is, an eight-membered ring binding species may be formed in aqueous media between allylic alcohol, sulfinic acid and water, while a six-membered ring binding species may be formed in common aprotic organic solvent between allylic alcohol and sulfinic acid. Both binding species may be accounted for the efficient activation of allylic alcohols via hydrogen bonding.

Palladium-Catalyzed Allylic Sulfinate-Sulfone Rearrangements

Upon treatment with a zero-valent palladium catalyst, tetrakis(triphenylphosphine)palladium, in tetrahydrofuran under mild conditions allylic p-toluenesulfinates underwent α- or γ-rearrangements of the sulfonyl group via ionic intermediates to give allylic sulfones.The regiochemistry of the rearrangements depends on the character of the intermediary allylic cationic carbons generated and the steric hindrance involved therein.Keywords - allylic sulfinate; allylic sulfone; palladium catalyst; sulfinate-sulfone rearrangement; regiochemistry; tetrakis(triphenylphosphine)palladium.

Convenient Methods for the Preparation of Vinylic and Allylic Sulfones from Alkenes, Haloalkanes, and Aldehydes. Stereochemistry of the Conversion of Vinylic Sulfones to the Corresponding Allylic Sulfones

1- or 2-p-Tolylsulfonyl(=tosyl)-1-alkenes, vinylic sulfones, were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration and also from 1-haloalkanes by the homologation or unhomologation methods.The vinylic sulfones thus prepared were further converted to the corresponding allylic sulfones under basic conditions.The stereochemistry of this conversion was discussed.One-carbon homologated allylic sulfones were directly obtained from aldehydes in good yields by the reaction with diethyl phenylsulfonylmethylphosphonate and 1,8-diazabicycloundec-7-ene (DBU) under mild conditions.

CONVENIENT METHODS FOR THE PREPARATION OF VINYLIC AND ALLYLIC SULFONES FROM ALKENES

1 or 2-p-Toluenesulfonyl(=tosyl)-1-alkenes were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration, respectively.Conversion of 1-tosyl-1-alkenes to the corresponding allylic sulfones, 1-tosyl-2-alkenes, was achieved by t