71624-75-4

Upstream product

• 544-97-8 dimethyl zinc(II) 
• 85895-63-2 1,1-bis(phenylthio)-4-tert-butylcyclohexane 
• 930-69-8 sodium thiophenolate 
• 108-98-5 thiophenol 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 63031-67-4 4-(1,1-dimethylethyl)cyclohexen-1-yltrimethylsilane 
• 119061-98-2 1-(tributylstannyl)-4-tert-butylcyclohexene 

Downstream Products

• 85894-99-1 dimethyl (2-(phenylthio)-5-tert-butyl-1-cyclohex-3-yl)malonate 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 63031-67-4 4-(1,1-dimethylethyl)cyclohexen-1-yltrimethylsilane 
• 151477-56-4 (4-tert-Butyl-cyclohex-1-enesulfonyl)-benzene 
• 102108-86-1 S-phenyl 4-tert-butyl-6-oxohexanethioate 
• 102108-87-2 (E)-5-tert-butyl-2-(phenylthio)cyclohexanone 
• 102108-87-2 (Z)-5-tert-butyl-2-(phenylthio)cyclohexanone 
• 85895-45-0 6-bromo-4-tert-butyl-1-(phenylthio)cyclohex-1-ene 
• 85895-46-1 2-bromo-1-(phenylthio)-4-tert-butylcyclohex-1-ene 

Relevant academic research and scientific papers

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.

REACTIONS OF VINYLSILANES WITH LEWIS ACID-ACTIVATED IODOSYLBENZENE: STEREOSPECIFIC SYNTHESIS OF VINYLIODONIUM TETRAFLUOROBORATES AND THEIR REACTIONS AS HIGHLY ACTIVATED VINYL HALIDES

Alkenyl(phenyl)iodonium tetrafluoroborates 3 were synthesized from alkenylsilanes 1 by the reaction with iodosylbenzene and boron trifluoride-diethyl ether or triethyloxonium tetrafluoroborate.The reaction proceeds stereospecifically with retention of configuration of 1.X-ray diffraction analysis of (4-tert-butylcyclohexenyl)phenyliodonium tetrafluoroborate (3b) revealed the highly ionic structure with the distorted T-shape arrangement.Iodonium salts 3 behave like the highly activated species of vinyl iodides due to the high leaving ability of the iodine(III) substituents.Thus, a variety of substituted olefins including α-cyano and α-nitro olefins, vinyl sulfides, vinyl halides and α,β-unsaturated esters, were synthesized from 3 under mild conditions.A ligand coupling mechanism via the formation of 10-I-3 intermediate 27 containing a copper(III) ligand is proposed for the substitutions of 3 with nucleophiles.

NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 74. LITHIUM TRIMETHYLSILYLDIAZOMETHANE. A USEFUL REAGENT FOR THE PREPARATION OF PYRAZOLES FROM α,β-UNSATURATED SULFONES

Lithium trimethylsilyldiazomethane smoothly reacts with various α,β-unsaturated sulfones to give 3 (or 5)-trimethylsilylpyrazoles in excellent yields.

ORGANOMETALLICS IN ORGANIC SYNTHESIS. APPLICATIONS OF A NEW DIORGANOZINC REACTION TO THE SYNTHESIS OF C-GLYCOSYL COMPOUNDS WITH EVIDENCE FOR AN OXONIUM-ION MECHANISM

The mechanistic and stereochemical features of a new organozinc-based substitution process 1,R2)-SPh + R32Zn --> heteroatom-C-(R1,R2,R3)>, first discovered during a total synthesis of the alkaloid mycotoxin α-cyclopiazonic acid, are described.Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process.Since these sulfur compounds are converted into C-glycosyl compounds with some degree of stereoselectivity, the organozinc chemistry does provide a new entry to these biologically active substances.

VINYLIODONIUM SALTS: THEIR STEREOSPECIFIC SYNTHESIS AND REACTIONS AS THE ACTIVATED VINYL HALIDES

Vinyliodonium salts 2 were synthesized from vinylsilanes 1 by the reaction with iodosylbenzene and triethyloxonium tetrafluoroborate.The reaction occurs stereospecifically with retention of configuration.Vinyliodonium salts 2 are highly effective as the activated species of vinyl iodides.Thus, a variety of substituted olefins including α-cyano and α-nitro olefins, vinyl sulfides, vinyl halides, and α,β-unsaturated esters, were prepared from 2 under mild reaction conditions.

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.