NICKEL-CATALYZED REACTION OF SILACYCLOPROPENES WITH ACETYLENES. A CONVENIENT ROUTE TO 1-SILACYCLOPENTA-2,4-DIENES

Article abstract of DOI:10.1016/S0022-328X(00)86021-0

The reaction of 1-silacyclopropenes prepared photochemically from phenylethynyldisilanes with acetylenes in the presence of a nickel catalyst has been investigated.The reaction of 1,1-dimethyl-2-phenyl-3-trimethylsilyl-, 1,1-dimethyl-2-phenyl-3-phenyldimethylsilyl-, 1-methyl-1,2-diphenyl-3-trimethylsilyl-, 1,1,2-triphenyl-3-trimethylsilyl- and 1-methyl-1-mesityl-2-phenyl-3-trimethyl-silyl-1-silacyclopropene with a phenylsilylacetylene in the presence of NiCl2(PEt3)2 afforded the respective 2,5-bis(silyl)-3,4-diphenyl-1-silacyclopenta-2,4-dienes in high yields. 1-Methyl-1,3-bis(trimethylsilyl)-2-phenyl-1-silacyclopropene reacted with phenyl(trimethylsilyl)acetylene to give 1-methyl-1,2,5-tris(trimethylsilyl)-3,4-diphenyl-1-silacyclopenta-2,4-diene and isomers, while 1,1-dimesityl-2-phenyl-3-trimethylsilyl-1-silacyclopropene afforded no 1-silacyclopenta-2,4-diene.