81699-88-9

Upstream product

• 764-93-2 1-decyne 
• 2179-79-5 phenyl selenocyanate 
• 34837-55-3 Phenylselenyl bromide 
• 128736-52-7 benzeneselenenyl p-toluenesulfonate 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 350508-71-3 Toluene-4-sulfonic acid (Z)-1-phenylselanyl-dec-1-enyl ester 

Relevant academic research and scientific papers

A new synthesis of α-phenylseleno esters and acids from terminal alkynes

Alkynyl phenyl selenides, easily prepared from terminal alkynes, react with p-toluenesulfonic acid to afford (Z)-α-(phenylseleno)vinyl p-toluenesulfonates. The reactions of these compounds with phenylselenenyl sulfate in the presence of alcohols or water

Formation and Electrophilic Reactions of Benzeneselenenyl p-Toluenesulfonate. Perparation and Properties of Addition Products with Acetylenes

Benzeneselenenyl p-toluenesulfonate (1) was generated in situ by the reaction of silver p-toluenesulfonate with benzeneselenenyl chloride in acetonitrile.The reagent reacted with acetylenes by electrophilic 1,2-addition to afford the β-(phenylseleno)vinyl p-toluenesulfonates 2-12, generally in high yield.The latter were formed preferentially by anti addition, but with poor regioselectivity, unless a strongly orienting group (e.g., phenyl) was present.Selenenyl sulfonate 1 was also unexpectedly produced via radical pathways by heating p-toluenesulfonic acid with AIBN in the presence of diphenyl diselenide, or from the pyrolysis of sulfinyl sulfone 15 with the diselenide.The regioisomeric adducts 3 and 4 were prepared from 1 and 1-decyne, and both underwent elimination with potassium tert-butoxide to afford the acetylenic selenide 19 initially, which isomerized to a 6:1 mixture of the propargylic and allenic selenides 20 and 21 upon further equilibration.A Fritsch-Buttenberg-Wiechell rearrangement is proposed for the elimination of 4.The syn elimination of the selenoxide of 4 required forcing conditions and afforded only ca. 20percent of the corresponding allenic sulfonate 22.The electrophile 1 induced the efficient cyclization of 5-hexen-1-ol and 4-pentenoic acid to the corresponding pyran 24 and lactone 25, respectively.It failed to cyclize alkynols, but afforded the lactones 28 and 29 from 4-pentynoic acid in low yield.

THE REACTION OF TERMINAL ALKYNES WITH THE REAGENT PREPARED FROM BENZENESELENENYL BROMIDE AND SILVER NITRITE. NOVEL EFFICIENT SYNTHESIS OF 1-ALKYNYL PHENYL SELENIDES

1-Alkynyl phenyl selenides were synthesized in good yields by the reaction of 1-alkynes with a new reagent prepared from benzeneselenenyl bromide and silver nitrite.

Cu(I)-CATALYZED REACTION OF TERMINAL ALKYNES WITH PHENYL SELENOCYANATE IN THE PRESENCE OF TRIETHYLAMINE. SYNTHESIS OF ALKYNYL SELENIDES

Treatment of terminal alkynes with phenyl selenocyanate in dichloromethane in the presence of CuX(X=CN or Br) and triethylamine at room temperature gave 1-phenylseleno-1-alkynes in high yields.