77202-22-3

Upstream product

• 13522-48-0 3-(phenylthio)-but-3-en-2-one 
• 21300-30-1 lithium 1-cyclohexenolate 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 77202-27-8 3-(phenylthio)-3-buten-2-ol 
• 1822-73-7 phenylthioethylene 
• 931-59-9 benzenesulfenyl chloride 
• 108-94-1 cyclohexanone 
• 80485-53-6 phenyl α-bromovinyl sulfide 
• 83666-49-3 4a,5,6,7,8,8a-hexahydro-2-methyl-8a-(N-morpholino)-3-(phenylthio)-4H-chromene 

Downstream Products

• 1125-78-6 5,6,7,8-Tetrahydro-2-naphthol 
• 77202-24-5 phenyl-(5,6,7,8-tetrahydronaphthalen-2-yl)sulfane 
• 77202-25-6 9-hydroxy-Δ³⁽⁴⁾-2-octalone 
• 80485-55-8 8a-hydroxy-3-(phenylsulfonyl)-2-decalone 
• 119-64-2 tetralin 

Relevant academic research and scientific papers

Reactions of 3-(Phenylthio)-3-buten-2-one with Cycloalkanones. A New Approach to Fused Phenols

Synthesis and properties of 3-(phenylthio)-3-buten-2-one (7) have been described.The butenone 7 reacted with lithium cycloalkanone enolates to give ketols 14 or diketones 15 in good yields, which were easily transformed into fused phenols 17 by the treatment with p-toluenesulfonic acid or sodium ethoxide, respectively.Oxidative elimination of the sulfenyl group of 14a afforded also 2-naphthol 17a.Tetrahydronaphthalene 23, a key intermediate of calamenene 1a and calamenenal 1b, was successfully synthesized by this approach by starting from l-carvone (19).Bicyclooctanone 25 was obtained in the reaction of 7 with kinetic enolate of 2-cyclohexen-1-one in 84percent yield.

Cycloaddition Reactions of 3-(Phenylthio)-3-buten-2-one: Synthesis of Functionalized Dihydropyran Derivatives and Their Ring-Opening Reactions

3-(Phenylthio)-3-buten-2-one (1) reacted with nucleophilic olefins such as vinyl ethers, vinyl sulfide, and enamine to give 1,4-cycloaddition products and/or Michael adducts 7-17 in fairly good yields.Treatment of 2-acetyl-2,5-bis(phenylthio)-3,4-dihydro-6-methyl-2H-pyran (2) with various acids or mercury(II) chloride gave the cyclopentanone 19.In addition, the dimer 2 was converted into 3-(phenylthio)-7-octene-2,6-dione (23) by the three steps.

Annelation Reactions of 3-Phenylthiobut-3-en-2-one. A New Method of Constructing Fused Phenols

Reactions of 3-phenylthiobut-3-en-2-one with enolate anions of cyclohexanone and cyclopentanone gave good yields of 8a-hydroxy-3-phenylthio-2-decalone and 3a-hydroxy-6-phenylthiohexahydroindan-5-one which were readily converted into 5,6,7,8-tetrahydro-2-naphthol and indan-5-ol, respectively, on exposure to toluene-p-sulphonic acid: a similar reaction of the enolate of cycloheptanone and subsequent treatment with sodium ethoxide gave 2-hydroxy-5,6,7,8-tetrahydrobenzocycloheptene.