173382-69-9

Upstream product

• 583-53-9 2,3-dibromobenzene 
• 116510-22-6 1,2-bis(1-methylsulfonyloxyprop-1-yn-1-yl)benzene 
• 116510-02-2 1,2-bis(3-hydroxyprop-1-yn-1-yl)benzene 

Downstream Products

• 1400590-71-7 C₃₂H₃₄N₄O₈ 
• 1400590-73-9 C₂₂H₁₈N₄O₄ 

Relevant academic research and scientific papers

Effect of remote trigonal carbons on the kinetics of Bergman cyclization: Synthesis and chemical reactivity of pyridazinedione-based enediynes

The synthesis and chemical reactivity of pyridazinedione-based enediynes (1, 2) are described. Both of these enediynes, namely the dihydro compound 1 and its corresponding tetrahydro analogue 2, were prepared by double N,O-alkylation of the corresponding

Enediyne scaffold-based highly selective chemosensor for ratiometric sensing of H2PO4-ions

Enediyne scaffold - based new chemosensor 1 has been designed and synthesized. The sensor 1 fluorometrically recognizes H2PO4- in CH3CN containing 1% DMSO by exhibiting a ratiometric change in emission upon complexation. The associat

Synthesis and reactivity of enediyne-nucleobase hybrids: Effect of intramolecular π-stacking

Three distinct classes of nucleobase-containing enediynes 1-9 with varying nature of the linker have been synthesized to explore the effect of π-stacking interaction in accelerating the rate of Bergman cyclization (BC). Chemical reactivity study, both experimental and computations demonstrated the important role that aromatic π-stacking interactions between the appended nucleobases within an enediyne frame play in lowering the activation barrier of Bergman cyclization.

1,x-Elimination reactions: Extending the limits of a classical organic reaction

α,ω)-Dibromo derivatives in ich the two terminal carbon atom are separated by an unsaturated spacer unit (ππ spacer") undergo 1,x-elimination reactions (with x = 6, 8, 10, and 14), using Mori's reagent (nBu3SnSiMe3/CsF). The resulting cumulenic intermediates cyclodimerize in a subsequent step yielding novel macrocyclic acetylenic and bridged aromatic compounds (cyclophanes). Thus 1,6-eliminations were carried out with dibromide 17 to yield 1,3,7,9-cyclododecatetrayne (20) and with benzylbromide 24 to provide cyclophanes 26 and 27. By 1,8-eliminations the 16-membered macrocycle 33 could be prepared from enediyne 31, the benzannelated 1,5-cyclooctadiyne 41 from dibromide 38, and a mixture of cyclophanes 45 and 46 from the precursor 43. 1,10-Eliminations were carried out successfully with dibromides 47, 50, and 53 yielding the corresponding unsaturated cyclophanes ("cyclophynes") 49, 52, and 55. The influence of the solvent on the cyclodimerization 47→49 was investigated, with acetonitrile providing the highest yields. The heterophanes 59a and b were obtained by 1,10-elimination of the precursor dibromides 57 a and b, and in an elimination experiment involving a 1:1 mixture of the dibromides 50 and 57 b the "mixed dimer" 60 was isolated, besides the homodimers 52 and 59 b. The method reached its limits with the 1,14-elimination of 68, 70, and 74 providing the cyclophanes 69, 71, and 75 in varying amounts. Two final debrominations with 76 and 77, which in principle could undergo 1,16- and 1,20-eliminations reactions, respectively, failed. The structures of the new cyclophanes 49, 50, 59 a, and 59 b were established by X-ray structural analysis; all other structure assignments rest on the usual spectroscopic and analytical data.

Photoisomerization as a trigger for Bergman cyclization: Synthesis and reactivity of azoenediynes

Cyclic enediynes 1a and 2a containing stable E-azo moiety (azoenediynes) have been synthesized. These compounds upon irradiation with long wavelength UV isomerize to the Z-compounds 1b and 2b, which can be thermally reisomerized to the Z compounds. Reacti

para- und ortho-Chinodimethan-Zwischenstufen mit cumulierten Doppelbindungen

Keywords: Chinodimethane, Cumulene, Cyclophane