93731-78-3

Upstream product

• 487-68-3 mesytaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 82988-76-9 mesityl diazomethane 
• 100879-90-1 1,3,5-trimethyl-2-pentyl-benzene 
• 17024-57-6 2,4,6,2',4',6'-hexamethyl-trans-stilbene 
• 27645-05-2 3-mesitylpropanenitrile 
• 76062-74-3 N,N'-Bis-[1-(2,4,6-trimethyl-phenyl)-meth-(E)-ylidene]-hydrazine 
• 4214-39-5 (Z)-1,2-dimesitylethene 
• 487-68-3 mesytaldehyde 
• 75142-57-3 2-(fluoromethyl)-1,3,5-trimethylbenzene 
• 96174-59-3 2,4,6-Trimethyl-benzaldehyd- 
• 94678-96-3 2,4,6-trimethylbenzaldehyde azine 

Relevant academic research and scientific papers

Laser flash photolysis study of phenylcarbene, o-tolylcarbene and mesitylcarbene

Laser flash photolysis (LFP, XeCl, 308 nm, 20 ns) of phenyldiazomethane (PDM), o-tolydiazomethane (TDM) and mesitydiazomethane (MDM) produces phenylcarbene (PC), o-tolycarbene (TC) and mesitylcarbene (MSC), respectively. Transient spectra of PC and TC cou

An easy access to fluoroalkanes by deoxygenative hydrofluorination of carbonyl compounds via their tosylhydrazones

An efficient and operationally simple synthesis of fluoroalkanes by deoxygenative hydrofluorination of carbonyl compounds via their tosylhydrazone surrogates is reported. The reaction can be carried out in a one-pot procedure directly from carbonyl compounds.

Catalytic asymmetric epoxidation of aldehydes. Optimization, mechanism, and discovery of stereoelectronic control involving a combination of anomeric and cieplak effects in sulfur ylide epoxidations with chiral 1,3-oxathianes

A range of 1,3-oxathianes based on camphorsulfonic acid have been prepared and tested in the catalytic asymmetric epoxidation of carbonyl compounds. It was found that the 1,3-oxathiane derived from acetaldehyde 5b gave the highest yield and enantioselectivity in the epoxidation process. The enantioselectivity was independent of the solvent and metal catalyst used (although yields were dependent on both). The optimum conditions were applied to a range of aldehydes, and good enantioselectivities and diastereoselectivities were observed. The origin of the enantioselectivity was probed, and in particular the role of the oxygen of the 1,3-oxathiane was investigated. Thus, the sulfur and carbon analogues of the camphorsulfonic acid based 1,3-oxathiane (derived from formaldehyde) were prepared (i.e., 1,3-dithiane and thiane analogues). With this series of analogues the steric effects are minimized so that the electronic effects can be investigated. The series of compounds was reacted in the catalytic cycle with benzaldehyde and gave stilbene oxides with 44% ee (sulfur analogue), 41% ee (1,3-oxathiane), and 20% ee (carbon analogue). Thus, it was concluded that the oxygen of the 1,3-oxathiane exerted a significant electronic effect in controlling the face selectivity of the ylide reactions. This electronic effect was a result of combined anomeric (higher with the sulfur analogue, not present with the carbon analogue) and Cieplak effects. A strong anomeric effect was observed in the X-ray structures of one of the 1,3-oxathianes, and an even greater one was observed in the corresponding sulfoxide (this was used as an electronic analogue of the ylide). The face selectivity of the ylide was believed to be complete in reactions with 5b. The minor enantiomer resulted from reaction of the minor conformer of the ylide, reacting again with high face selectivity. This was proven by using a more substituted diazo compound, which was expected to give much less of the minor conformer. Indeed, reaction with mesityldiazomethane gave the corresponding epoxide in essentially enantiomerically pure form.

Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes

(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.

THE SYNTHESIS OF ARYL DIAZOMETHANES

A convenient and rapid method for preparing aryldiazomethanes from the related tosylhydrazones employing phase transfer catalysis with hydrocarbon solvents in good to excellent yields has been developed.