60164-94-5

Upstream product

• 75-25-2 Bromoform 
• 589-92-4 1-methylcyclohexan-4-one 
• 77842-31-0 (aR)-(-)-(4-methylcyclohexylidene)acetic acid 
• 127180-76-1 ethyl 4-methylcyclohexylideneacetate 
• 96554-93-7 1-Methyl-4-((R)-4-methyl-cyclohexylmethanesulfinyl)-benzene 
• 96493-66-2 1-[(R)-(R)-Bromo-(4-methyl-cyclohexyl)-methanesulfinyl]-4-methyl-benzene 

Downstream Products

• 60164-97-8 bis-1,2-(4-methylcyclohexylidene)ethane 
• 91296-37-6 (αS)-(-)-(4-methylcyclohexylidene)deuteriomethane 
• 296269-03-9 1-methyl-4-(trimethylsilylmethylene)cyclohexane 
• 369628-38-6 (SR)-1-dimethylphenylsilylmethylene-4-methylcyclohexane 
• 79464-57-6 (aS)-(4-methylcyclohexane)ethylidene 
• 79464-57-6 (4-methylcyclohexylidene)ethane 
• 60164-99-0 (+)-(S)-(4-Methylcyclohexylidene)ethane 
• 369628-40-0 (SR)-1-dimethylphenylsilyloxymethylene-4-methylcyclohexane 
• 369625-85-4 dimethyl-(6-methyl-1-oxa-spiro[2.5]oct-2-yl)-phenyl-silane 

Relevant academic research and scientific papers

A new entry of highly nucleophilic CHBr3-TiCl4-Mg system for the stereoselective synthesis of 1-alkenyl bromides

This TiCl4-Mg promoted coupling of CHBr3 with various aldehydes and ketones, especially in sterically hindered or enolizable ketones, provides a simple, practical, and stereoselective carbonyl-bromomethylenation leading primarily to (E)-vinyl bromides.

Solvolysis of chiral cyclohexylidenemethyl triflate. Evidence against a primary vinyl cation intermediate

Solvolysis of (R)-4-methylcyclohexylidenemethyl triflate (6) was examined at 140°C in various aqueous methanol and some other alcoholic solvents. The main product was (R)-4-methylcycloheptanone that maintains the stereochemical purity of 6, with accompanying 4-methylcyclohexanecarbaldehyde. In the presence of bromide ion, the bromide substitution product was also obtained, mostly with inversion of configuration. It is concluded that the solvolysis does not involve the formation of the primary vinyl cation but proceeds via σ-bond participation to form the rearranged cycloheptenyl cation as an intermediate. Copyright

Solvolysis of optically active 4-methylcyclohexylidenemethyl triflate: Evidence against a primary vinyl cation as an intermediate

Solvolysis of (R)-4-methylcyclohexylidenemethyl triflate in aqueous methanol at 140 °C gave stereospecifically (R)-4-methylcycloheptanone to definitively rule out intermediate formation of the achiral primary vinyl cation. The rearrangement must occur via concerted σ-bond participation.

ENANTIOSPECIFIC SYNTHESIS OF OPTICALLY ACTIVE CYCLOHEXYLIDENE BROMOMETHANES

Optically pure cyclohexylidene bromomethanes were prepared by stereospecific bromination alpha to a chiral sulfoxide, followed by the stereospecific pyrolytic elimination of the sulfoxide moiety.

ELECTRON TRANSFER FROM METAL SURFACES. FORMATION OF LITHIUM AND GRIGNARD REAGENTS.

Chiral (+)-(S)-4-methylcyclohexylidenebromomethane (1) has been prepared from (-)-(R)-4-methylcyclohexylideneacetic acid by a stereospecific bromodecarboxylation reaction.The reaction was shown to proceed with an overall inversion of configuration.The rea