52113-72-1

Upstream product

• 25632-03-5 1,1-dimethoxycyclooctane 
• 17314-33-9 tributyltin phenyl sulfide 
• 502-49-8 cycloactanone 
• 108-98-5 thiophenol 
• 7422-06-2 (Z)-3-bromocyclooct-1-ene 
• 882-33-7 diphenyldisulfane 
• 85895-35-8 1,1-bis(phenylthio)cyclooctane 

Downstream Products

• 85895-16-5 (Z)-1-Bromo-2-phenylsulfanyl-cyclooctene 
• 128803-27-0 Cyclohexyl-((E)-cyclooct-1-enyl)-methanol 
• 96308-48-4 cyclooctene-1-carbaldehyde 
• 143741-66-6 2-phenylthio-3-chloro-1,3-cyclononadiene 

Relevant academic research and scientific papers

Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters

Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.

A Simple Method for Producing Cycloalkenyllithiums from Cycloalkanones via Reductive Lithiation of Enol Phenyl Thioethers

Cyclohexenyl, cycloheptenyl, and cyclooctenyl phenyl sulfides, readily prepared from the corresponding cycloalkanones, are reductively lithiated by lithium p,p'-di-tert-butylbiphenylide to produce cycloalkenyllithiums in good yields.

Clay Catalysis: A Simple and Efficient Synthesis of Enolthioethers from Cyclic Ketones

Montmorillonite KSF in refluxing toluene catalyses the synthesis of 1-alkyl- and 1-arylthioalkenes from ketones and thiols (thiophenol or 1-butanethiol).

Organotin-Mediated Preparation of Monothioacetals

Monothioacetals are obtained by treating the corresponding acetals with organotin thiophenoxides in the presence of BF3*OEt2.The reaction proceeds under mild conditions to provide the desired compounds with high selectivity.

ENOL THIOETHERS AS ENOL SUBSTITUTES. AN ALKYLATION SEQUENCE.

Ionic bromination of enol phenyl thiolethers forms predominantly to exclusively 2-(phenylthio)-3-bromo-1-alkenes, an enolonium equivalent. The allylic bromide participates in displacements with stabilized and nonstabilized nucleophiles. The ability to hydrolyze the enol thioethers to their corresponding ketones equates this sequence to an equivalence of an enolonium ion. The versatility of the sulfur in selective introduction of allylic hydroxyl and amino groups as well as the ability to directly replace the sulfur substituent by hydrogen or alkyl imparts special significance to this approach. The sequence is highly regio-and chemoselective. Applications include the synthesis of lanceol and bisabolene and the introduction of steroid side chains.