153140-77-3

Upstream product

• 693-02-7 hex-1-yne 
• 153140-75-1 1-bromo-2-[(Z)-2-bromoethenyl]benzene 

Downstream Products

• 163015-97-2 C₂₈H₃₀Se₂ 
• 163015-91-6 C₂₈H₃₀Te₂ 
• 1026886-57-6 ((Z)-2-Oct-1-en-3-ynyl)-benzenethiol 
• 207741-30-8 2-n-butyl-1,1-di-n-butyl-1-benzostannepine 
• 292614-18-7 bis[(Z)-o-(oct-1-en-3-ynyl)phenyl]di-n-butylstannane 
• 457885-27-7 bis[2-((1Z)-1-octen-3-ynyl)phenyl]acetylene 
• 457885-25-5 1-iodo-2-[(1Z)-1-octen-3-ynyl]benzene 

Relevant academic research and scientific papers

Synthesis of [5]-, [6]-, and [7]helicene via Ni(0)- or Co(I)-catalyzed isomerization of aromatic cis,cis-dienetriynes

An original approach to helicene frameworks exploiting atom economic isomerization of appropriate energy-rich aromatic cis,cis-dienetriynes has been developed. The new paradigm provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key cis,cis-dienetriynes and their nickel(0)-catalyzed [2+2+2] cycloisomerization. The potential of the methodology is underlined by the syntheses of the parent [5]helicene (2), 7,8-dibutyl[5]helicene (23), [6]helicene (24), and [7]helicene (25). The approach can be adapted to prepare functionalized helicenes as exemplified by the eight-step synthesis of 7,8-dibutyl-2,3-dimethoxy[6]helicene (34). Density functional theory (DFT) calculations showed that bis[2-((1Z)-1-buten-3- ynyl)phenyl]acetylene (1) and isomeric [5]helicene (2) differ enormously in the Gibbs energy content (ΔG= -136.6 kcal.mol-1) to favor highly the devised intramolecular simultaneous construction of three aromatic rings.

Studies on seven-membered heterocycles. XXXV). Synthesis of the group 16 1-benzoheteroepines involving the first examples of 1-benzotellurepine and 1-benzoselenepine rings

Novel 2-alkyl-1-benzotellurepines (11) and 2-alkyl-1-benzoselenepines (12) were obtained by sodium borohydride reduction of di[o-(1-buten-3-ynyl)phenyl] ditellurides (8) and diselenides (9), together with 2-alkylidene-2H-tellurachromenes (13) and 2-alkylidene-2H-selenachromenes (14), respectively, via the phenyltellurol and phenylselenol intermediates (10). The dimers (8, 9) were readily prepared from the 4-alkyl-1-(o-bromophenyl)-1-buten-3-ynes (7) by successive treatment with tert-butyllithium, tellurium or selenium powder, and potassium ferricyanide in one pot. The 2-alkyl-1-benzothiepines (16) were obtained directly from the enynes (7) by successive treatment with tert-butyllithium, sulfur powder, and ethanol in one pot. To examine the chemical behavior of the novel tellurepine ring, several reactions of 2-tert-butyltellurepine (11c) were carried out.

Synthesis of the First Examples of 1-Benzotellurepines and 1-Benzoselenepines

The novel 2-alkyl-1-benzotellurepines 8 and 2-alkyl-1-benzoselenepines 9 have been obtained by sodium borohydride reduction of the ditelluride 4 and diselenide dimers 5, prepared from 4-alkyl-1-(o-bromophenyl)but-1-en-3-ynes 3 via three steps in one pot,