131190-11-9

Upstream product

• 14267-92-6 1-chloro-4-pentyne 
• 34097-60-4 methyl benzenesulfonylacetate 
• 68275-03-6 pent-4-yn-1-yl methanesulfonate 

Downstream Products

• 131190-07-3 2-benzylidenecyclopentane-1,1-dicarboxylic acid dimethyl ester 
• 131190-15-3 (E)-2-benzylidene-1-methoxycarbonyle-1-phenylsulfonyle cyclopentane 
• 141236-32-0 1-(methoxycarbonyl)-1-(phenylsulfonyl)-2-methylenecyclopentane 
• 138770-04-4 1-Benzenesulfonyl-2-hept-2-yn-(E)-ylidene-cyclopentanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

The synthesis of (E)-arylidene and allylidene cyclopentanes by means of a pallodium(0)-catalyzed complex

When treated with an unsaturated halide in a palladium-catalyzed process, the anions from γ-acetylenic malonates 4 and 5 stereospecifically lead to cyclopentanes having an exo tri- or tetra-substituted double bond. This reaction which forms simultaneously two carbon-carbon bonds is believed to proceed by nucleophilic attack of the anion on the triple bond activated by the σ-aryl or σ-vinyl palladium complex.

Stereospecific synthesis of arylidene and allylidene cyclopentanes by a palladium-catalyzed cylisation

Vinyl and aryl halides react with ε-acetylenic β-diesters, β-keto esters and βsulfonylesters in the presence of a Pd(o) catalyst leading in good yields to the title compounds. The acetylenic homolog containing an additional carbon leads in the same conditions to a cyclohexane, but this process then competes with the arylation of the terminal acetylenic carbon.