124828-72-4

Upstream product

• 67-56-1 methanol 
• 124828-68-8 1-(4-methoxyphenyl)-1,1-diphenylhept-2-yne 
• 124828-69-9 1,1,1-tris-(4-methoxyphenyl)hept-2-yne 
• 137836-08-9 1,4-Bis<1,1-bis(p-methoxyphenyl)hept-2-ynyl>benzene 
• 32359-01-6 hexenylmagnesium bromide 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 115085-23-9 1-(4-methoxyphenyl)hept-2-yn-1-ol 
• 123-11-5 4-methoxy-benzaldehyde 
• 693-02-7 hex-1-yne 
• 49757-42-8 4,4',4''-trimethoxytrityl chloride 

Relevant academic research and scientific papers

HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols

The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C-O, C-N and C-C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid loading (typically 1 mol-%) under simple reaction conditions. The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C-O, C-N and C-C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol-%) under mild reaction conditions.

Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives

A wide range of primary, secondary and tertiary propargylic alcohols undergo a Meyer-Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4-methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined in a one-pot procedure with the addition of a nucleophile to the resulting terminal enone, to give β-aryl, β-alkoxy, β-amino or β-sulfido ketones. Propargylic alcohols bearing an adjacent electron-rich aryl group can also undergo silver-catalyzed substitution of the alcohol with oxygen, nitrogen and carbon nucleophiles. This latter reaction was initially observed with a batch of gold catalyst that was probably contaminated with small quantities of silver salt.

Photolyses of 1,4-Bis(1,1-diarylhept-2-ynyl)benzenes and 1,4-Bis(1,1-diarylalkyl)benzenes

Photolyses of 1,4-bis(1,1-diarylhept-2-ynyl)benzenes or 1,4-bis(1,1-diarylalkyl)benzenes 2 in a tetrahydrofuran-methanol mixture gave 1-biphenyl-4-yl-1,1-diarylhept-2-ynes or 1-biphenyl-4-yl-1,1-diarylalkanes 3 as major products and biaryls 1 as minor products.The products 3 were obtained with quantum yields of 0.010-0.020, respectively.

Photolysis of 1,1,1-Triarylalk-2-enes and 1,1,1-Triarylhept-2-ynes. A Novel Generation of Aryl(alk-1-enyl)carbenes ans Aryl(alk-1-ynyl)carbenes

Upon UV irradiation in methanol, 1,1,1-triarylhept-2-ynes underwent an α,α-elimination of two aryl groups to give a biaryl and the corresponding carbene which reacted with methanol to give a 1-aryl-1-methoxyhept-2-yne. 1,1,1-Triphenylalk-2-enes underwent α,α-elimination of two phenyl groups and also elimination of an alkene and a phenyl group to give biphenyl and a 1-phenylalkene respectively.In both cases, the corresponding carbenes were formed and were isolated as methanol insertion products (a 1-methoxy-1-phenylalk-2-ene and diphenylmethyl methyl ether, respectively).A rearrangement product, a 1,1,2-triphenylcyclopropane, was also formed.

Photolysis of 1,1,1-Triarylhept-2-ynes. Generation of Phenyl(hex-1-ynyl)carbene

Photolysis of 1,1,1-triarylhept-2-yne in methanol gave biaryl and 1-aryl-1-methoxyhept-2-yne, which may be derived from the insertion of aryl(hex-1-ynyl)carbene into the OH bond of methanol.The carbene may be generated by photo-α,α-elimination of two aryl groups from the substrate.