31162-76-2

Upstream product

• 19451-55-9 Neryl diphenyl phosphate 
• 930-69-8 sodium thiophenolate 
• 106-25-2 Nerol 
• 882-33-7 diphenyldisulfane 
• 62252-44-2 2-(3,7-Dimethylocta-2,6-dienyl)-oxy-3,5-dinitropyridin 
• 108-98-5 thiophenol 
• 5219-61-4 (phenylthio)acetonitrile 
• 77411-98-4 3,7-dimethyl-2-(phenylthio)-1-(trimethylsilyl)oct-6-en-3-ol 
• 61829-54-7 2-(phenylthio)-1-(trimethylsilyl)butan-3-one 
• 61829-51-4 2-(phenylthio)-3-(trimethysilyl)propanenitrile 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 77411-99-5 3,7-dimethyl-3-phenylthio-octa-1,6-diene 
• 124-63-0 methanesulfonyl chloride 
• 72863-23-1 3,7-dimethyl-3-(p-tolylsulfonyl)-1,6-octadiene 

Downstream Products

• 83577-63-3 (2,6-dimethyl-2-vinylhept-5-enyl)(phenyl)sulfane 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 172215-51-9 N-[3,7-dimethyl-1,6-octadien-3-yl]toluenosulfonamide 
• 128266-13-7 benzyl ether of 10,14-dimethyl-5-hydroxy-6-formylpentadeca-9Z,13-dien-1-ol 
• 128266-14-8 benzyl ether of 10,14-dimethyl-6-hydroxymethylpentadeca-5E,9Z,13-trien-1-ol 
• 245514-65-2 (Z)-(R)-2-[(2S,5R)-5-((Z)-(S)-1-Hydroxy-1,5,9-trimethyl-3-phenylsulfanyl-deca-4,8-dienyl)-tetrahydro-furan-2-yl]-6,10-dimethyl-4-phenylsulfanyl-undeca-5,9-dien-2-ol 
• 125556-26-5 (Z)-6,10-Dimethyl-4-phenylthio-5,9-undecadienal ethylene acetal 

Relevant academic research and scientific papers

Highly selective sulfoxidation of allylic and vinylic sulfides by hydrogen peroxide using a flavin as catalyst

A highly chemoselective oxidation of allylic and vinylic sulfides to the corresponding sulfoxides has been developed using flavin 1 as the oxidation catalyst and hydrogen peroxide as the terminal oxidant. The sulfoxides were formed in good to excellent yields in a highly selective manner even when an excess of the oxidant was used. Sulfone formation was completely suppressed to 0.5% (in one single case 1.5% sulfone was detected). No epoxidation of double bonds or interference with other functional groups was observed under the reaction conditions. The general applicability was demonstrated by the selective oxidation of various allylic and vinylic sulfides having different electronic properties. A number of functionalities including hydroxy, acetoxy, amino, silyloxy, and formyl groups are tolerated under these mild reaction conditions.

Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

Reaction of allyl aryl sulfides and α-diazoacetic acid esters in the presence of optically active Co(III)-salen complex (8-Br) provided 3- substituted 2-arylthio-4-pentenoic acid esters stereoselectively by way of enantioselective S-ylide formation and subsequent diastereoselective [2,3]sigmatropic rearrangement. For example, the reaction of cinnamyl phenyl sulfide and (-)-menthyl α-diazoacetate provided (-)-menthyl (2R,3S)-2- phenylthio-3-phenyl-4-pentenoate of 74% de preferentially.

Effective combination of two-directional synthesis and rhenium(VII) chemistry: Total synthesis of meso polyether teurilene

The efficient total synthesis of the cytotoxic meso polyether teurilene (1), rarely occurring in nature, has been achieved through the effective combination of the concept of two-directional synthesis and the rapidly progressing rhenium(VII) chemistry. In

Direct synthesis of allyl sulfides from allyl alcohols and thiols

In the presence of boron trifluoride-diethyl ether complex, various allyl alcohols [(-)-myrtenol, geraniol, cinnamyl alcohol, linalool, 1-octen-3-ol, 2-hydroxybenzyl alcohol and bicyclic diols] were reacted with thiophenol, 1-butanethiol, trimethyl(phenylthio)silane or hexamethylsilane in dichloromethane at room temperature to give the corresponding allyl sulfides in good to excellent yields. The mild conditions for this transformation allowed chemoselectivity.

Organic Synthesis with sulfones. XLI. Nucleophilic substitution of allylic sulfones

The sulfonyl group in allylic sulfones can be displaced by a variety of nucleophiles.The reaction is particularly easy with tertiary sulfones, i.e. bearing no hydrogen atoms at the α-position.Lewis acids catalyse the displacement reaction.

The Formation of Allyl Sulphides by Phenylthio-migration: Control by Silicon

When γ-silyl-β-phenylthio-alcohols are treated with acid, the strategically placed silyl group encourages the rearrangement of the phenylthio-group, both from a secondary migration origin to a secondary migration terminus, and from a secondary migration origin to a tertiary migration terminus (4)->(6).Geraniol/nerol (12) and linalool (14) have been synthesised from a common intermediate (11) using this type of reaction.Phenylthio-migration from a tertiary migration origin (17)->(3) can be controlled to a limited extent by a suitably placed silyl group, but it is easier to achieve direct β-elimination of the silyl and phenylthio-groups (17)->(18).

Reaction of Allyl Diphenyl Phosphates with Soft Bases

The title phosphates were found to react with a variety of soft bases to give nucleophilic substitution products in high yields.The reaction proceeded regiospecifically under mild reaction conditions with preservation of the double bond geometry.