55983-32-9

Upstream product

• 5700-44-7 1-phenyl-1-cyclohexylethylene 
• 54774-82-2 (1-(cyclohex-1-en-1-yl)ethyl)benzene 
• 90334-41-1 N-Cyclohexylidene-N'-trityl-hydrazine 
• 98-86-2 acetophenone 
• 4352-39-0 1-cyclohexyl-1-phenylethanol 
• 108-94-1 cyclohexanone 
• 24379-49-5 (trimethylsilyl)phenyldiazomethane 
• 712-50-5 Cyclohexyl phenyl ketone 
• 74-88-4 methyl iodide 
• 144-62-7 oxalic acid 
• 931-51-1 cyclohexylmagnesiumchloride 
• 5664-20-0 vinylidenecyclohexane 
• 591-50-4 iodobenzene 
• 5769-02-8 2-methyl-2-phenyl[1,3]dithiolane 

Downstream Products

• 78775-39-0 1,1-Dichlor-2-methyl-2-phenylspiro<2.5>octan 
• 92862-83-4 1-(1-phenylvinyl)cyclohexanol 
• 521275-91-2 8-chloro-2-phenyloct-1-en-3-one 
• 521275-61-6 1-(1-phenylvinyl)cyclohexyl hydroperoxide 

Relevant academic research and scientific papers

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Iron-promoted elimination of β-thioalkoxy alcohols. Olefination by coupling of a carbonyl group with a dithioacetal

Treatment of propargylic dithiolanes with nBuLi followed by a carbonyl electrophile yields the corresponding propargylic dithioacetals. Upon treatment with 1 equiv of Fe(BCaC)3 and excess MeMgl, elimination of SR and OH moieties from 8 affords the corresponding olefins in satisfactory yield. Benzylic dithioacetals behave similarly. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents.

Regio- and stereoselective hydrostannation of allenes using dibutyliodotin hydride (Bu2SnIH) and successive coupling with aromatic halides

Regio- and stereoselective hydrostannation of allenes by using di-n-butyliodotin hydride (Bu2SnIH) was accomplished to give α,β-disubstituted vinyltins, which induced the synthesis of multi-substituted alkenes in a one-pot procedure. The Royal Society of Chemistry.

Insights into the general and efficient cross McMurry reactions between ketones

The selective cross McMurry couplings of diaryl or aryl ketones with various substituted ketones were achieved in 53-94% isolated yields. It is believed that the strong affinity of the substituents to the low-valent titanium surface plays an important role in regards to moderating selectivity. Through the introduction of such substituents followed by their removal post McMurry coupling, structurally similar ketones can be effectively cross-coupled.

Silica Chloride (SiO2-Cl) and Trimethylsilyl Chloride (TMSCl) Promote Facile and Efficient Dehydration of Tertiary Alcohols

Silica chloride (SiO2-Cl), as a heterogeneous reagent, has been used for the efficient dehydration of tertiary alcohols under mild reaction conditions. For comparison, we have also used trimethylsilyl chloride (TMSCl) as a homogeneous reagent for this purpose. We have found that silica chloride is a more efficient reagnet than trimethylsilyl chloride for this purpose. Handling of SiO2-Cl is much safer and easier than TMSCl, especially for large-scale operation. The selectivity of the method is also demonstrated by several competitive reactions. Ether formation, rearranged products, and polymerization have not been observed in the reactions.

AZO ANIONS IN SYNTHESIS. USE OF TRITYL- AND DIPHENYL-4-PYRIDYLMETHYLHYDRAZONES FOR REDUCTIVE C-C BOND FORMATION.

The lithium salts of trityl- and diphenyl-4-pyridylmethyl-hydrazones of both aldehydes and ketones react with electrophiles (alkyl halides, aldehydes, ketones, crotonates) at low temperature to form C-trapped azo compounds; these intermediates decompose homolytically with loss of nitrogen below room temperature and can be diverted in a synthetically useful way to alkanes, alkenes, alcohols or saturated esters.

Synthesis and Ring Cleavage of Highly Substituted 1,1-Dichloro- and 1-Bromo-1-fluorocyclopropanes

The tri- and tetrasubstituted olefines 1, 2, 4, 7 - 15, and 19 react with CCl2 to give the dichlorocyclopropanes 22, 23, 25, 26a - 30a, and 33a - 37a in high yield, while the highly sterically hindered olefins 5, 6, and 21 show no reaction.In a few border