33432-54-1

Upstream product

• 115-19-5 2-methyl-but-3-yn-2-ol 
• 583-53-9 2,3-dibromobenzene 
• 33432-48-3 1,2-Bis-[3-(1-ethoxy-ethoxy)-3-methyl-but-1-ynyl]-benzene 
• 615-42-9 1,2-Diiodobenzene 

Downstream Products

• 334868-25-6 1,2-bis(3-hydroxy-1-butynyl)benzene 
• 334868-09-6 1,2-bis(1-butyn-3-onyl)benzene 
• 334868-10-9 3-(2-(ethoxycarbonylethynyl)phenyl)prop-2-ynoic acid ethyl ester 
• 848567-81-7 1,2-bis(2,2':6',2''-terpyridin-4-yl-ethynyl)benzene 
• 21792-52-9 1,2-diethynylbenzene 

Relevant academic research and scientific papers

Construction of triangular metallomacrocycles: [M3(1,2-bis(2, 2′:6′,2″-terpyridin-4-yl-ethynyl)benzene)3] [M = Ru(II), Fe(II), 2Ru(II)Fe(II)]

Complexation of a predesigned (1,2-bis(2,2′:6′,2″- terpyridin-4-yl-ethynyl)benzene) ligand possessing a 60° angle between two terpyridines with transition metals [Fe(II) and Ru(II)] afforded the self-assembled, triangular metallomacrocycles. The Royal Soc

Tuning Rate of the Bergman Cyclization of Benzannelated Enediynes with Ortho Substituents

matrix presented The Bergman cyclization of benzannelated enediynes is highly sensitive to ortho substitution. This finding opens possibilities for the rational design of conformer-specific and pH-dependent DNA-cleaving agents.

Carbonyl- and carboxyl-substituted enediynes: Synthesis, computations, and thermal reactivity

The influence of electron-withdrawing groups (carbonyl and carboxyl) at the alkyne termini on the reactivity of enediynes was investigated by a combination of experimental and computational techniques. While the general chemical reactivity of such enediynes, especially if non-benzannelated, is increased markedly, the thermal cyclization, giving rise to Bergman cyclization products, is changed little relative to the parent enediyne system. This is evident from kinetic measurements and from density functional theory (DFT, BLYP/6-31G* + thermal corrections) computations of the experimental systems which show that the Bergman cyclization barriers slightly (3-4 kcal/mol) increase, in contrast to earlier theoretical predictions. The effect on the endothermicities is large (ΔΔHr = 7-12 kcal/mol). Hence, the increased reactivity of the substituted enediynes is entirely due to nucleophiles or radicals present in solution. This was demonstrated by quantitative experiments with diethylamine and tetramethyl piperidyl oxide (TEMPO) which both give fulvenes through 5-exo-dig cyclizations.

Convenient preparation of di- and tri-ethynylbenzenes by cleavage of 2-hydroxy-2-methylbut-3-yn-4-yl-benzenes with water miscible reagents

2-Hydroxy-2-methylbut-3-yn-4-yl-benzenes, readily available from bromobenzenes, are efficiently cleaved by the water-miscible reagents sodium 2-propoxide in 2-propanol, or potassium hydroxide in dioxan, which facilitatese isolation of volatile ethynylbenzenes.

A SHORT ROUTE TO DEHYDRO ANNULENES

A novel synthesis of dehydro annulenes from 1,2-dibromobenzene is based on selective Pd(0)-Cu(1) coupling reactions of aryl and vinyl halides with terminal acetylenes.