29379-48-4

Upstream product

• 920-39-8 isopropylmagnesium bromide 
• 76-83-5 trityl chloride 
• 1068-55-9 isopropylmagnesium chloride 

Downstream Products

• 96112-34-4 1,1,1-Tricyclohexyl-2-methyl-propan 
• 92-52-4 biphenyl 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 52067-39-7 1-methoxy-1-phenyl-2-methylpropane 

Relevant academic research and scientific papers

Synthesis of Trialkylamines with Extreme Steric Hindrance and Their Decay by a Hofmann-like Elimination Reaction

A number of amines with three bulky alkyl groups at the nitrogen, which surpass the steric crowding of triisopropylamine considerably, were prepared by using different synthetic methods. It turned out that treatment of N-chlorodialkylamines with organometallic compounds, for example, Grignard reagents, in the presence of a major excess of tetramethylenediamine offered the most effective access to the target compounds. The limits of this method were also tested. The trialkylamines underwent a dealkylation reaction, depending on the degree of steric stress, even at ambient temperature. Because olefins were formed in this transformation, it showed some similarity with the Hofmann elimination. However, the thermal decay of sterically overcrowded tertiary amines was not promoted by bases. Instead, this reaction was strongly accelerated by protic conditions and even by trace amounts of water. Reaction mechanisms, which were analyzed with the help of quantum chemical calculations, are suggested to explain the experimental results.

Photolysis of 1,1,1-Triarylalkane. A New Photochemical Carbene Generation Process

Upon UV irradiation in methanol some 1,1,1-triarylalkanes underwent an α,α-elimination of two aryl groups to give biaryls and the corresponding carbene intermediates, which inserted into the OH bond of the methanol to afford methyl ethers and/or underwent a 1,2-H shift to afford olefins.Furthermore, the efficieny of this elimination was highly dependent upon the bulkiness of the alkyl groups.

Photolysis of 1,1,1-triphenylalkanes

Photolysis of 1,1,1-triphenylalkane in methanol gave biphenyl, 1-methoxy-1-phenylalkane, and 1-phenylalkene. The generation of the carbene intermediate by photo α,α-elimination of two phenyl groups was presumed.