181874-55-5

Upstream product

• 176789-90-5 3,4-benzo-1,1,2,2-tetra(isopropyl)-1,2-disilacyclobut-3-ene 
• 1066-54-2 trimethylsilylacetylene 
• 2227-29-4 chlorodiisopropylsilane 
• 176789-93-8 1,2-bis(diisopropylsilanyl)benzene 
• 176789-94-9 1,2-bis(chloroisopropylsilanyl)benzene 
• 583-53-9 2,3-dibromobenzene 

Relevant academic research and scientific papers

Platinum-catalyzed reactions of 3,4-benzo-1,1,2,2-tetra(isopropyl)-1,2-disilacyclobut-3-ene with mono-and di-substituted alkynes

The reactions of 3,4-benzo-1,1,2,2-tetra(isopropyl)-1,2-disilacyclobut-3-ene (1) with phenylacetylene and 1-hexyne in the presence of a catalytic amount of (η2-ethylene)bis(triphenylphosphine)platinum(0) at 200°C for 24 h gave two types of 1: 1 adducts, 2-phenyl-and 2-butyl-substituted 5,6-benzo-1,1,4,4-tetra(isopropyl)-1,4-disilacyclohexa-2,5-diene and 2-benzylidene-and 2-pentylidene-substituted 4,5-benzo-1,1,3,3-tetra(isopropyl)-1,3-disilacyclopent-4-ene, respectively. With mesityl-and dimethylphenylsilylacetylene, 1 afforded 2-(mesityl)methylene-and 2-(dimethylphenylsilyl)methylene-4,5-benzo-1,1,3,3-tetra(isopropyl)-1,3-disilacyclopent-4-ene. A similar reaction of 1 with trimethylsilylacetylene produced an adduct arising from sp-hybridized C-H bond activation of the acetylene, together with a benzodisilacyclopentene derivative. The reaction of 1 with diphenylacetylene yielded a 2,3-diphenyl-5,6-benzodisilacyclohexa-2,5-diene derivative, while with methylphenylacetylene and 2-hexyne, 1 gave 2-benzylidene-and 2-butylidene-5,6-benzo-1,4-disilacyclohex-5-ene, along with the benzodisilacyclohexa-2,5-diene derivatives. Similar treatment of 1 with methyl(trimethylsilyl)acetylene produced a 5,6-benzo-2-(trimethylsilyl)methylenedisilacyclohexene derivative.

Palladium-catalyzed reactions of 1,1,2,2-tetraethyl-and 1,1,2,2-tetra(isopropyl)-3,4-benzo-1,2-disilacyclobut-3-ene with alkynes

The reactions of 3,4-benzo-1,1,2,2-tetra(isopropyl)-1,2-disilacyclobut-3-ene (2) with acetylene, phenylacetylene, 1-hexyne, and o-tolylacetylene in the presence of tetrakis(triphenylphosphine)palladium gave the respective 5,6-benzo-1,4-disilacyclohexa-2,5-dienes 3-6. Similar reactions of 2 with mesitylacetylene, trimethylsilylacetylene, and dimethylphenylsilylacetylene afforded 1-alkynyl(diisopropylsilyl)-2-(diisopropylsilyl)benzenes 7-9 arising from sp-hybridized C-H bond activation of acetylenes. The reactions of 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene with mesitylacetylene, trimethylsilylacetylene, and dimethylphenylsilylacetylene produced 5,6-benzo-1,4-disilacyclohexa-2,5-dienes 10-12 as the sole product. The stoichiometric reaction of 2 with tetrakis(triphenylphosphine)palladium gave a yield of 3,4-benzo-2,2,5,5-tetra(isopropyl)-1-pallada-2,5-disilacyclopent-3-ene (A), arising from insertion of a palladium species into a silicon-silicon bond in 2.