TY - JOUR
T1 - Palladium- and platinum-catalyzed reactions of benzo[1,2:4,5]bis(1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene) with alkenes
AU - Naka, Akinobu
AU - Koo Lee, Kyung
AU - Yoshizawa, Kazunari
AU - Yamabe, Tokio
AU - Ishikawa, Mitsuo
N1 - Funding Information:
This work was partially supported by Grant-in-Aid for Scientific Research on Priority Areas (No. 10133257) from the Ministry of Education, Science, Sports and Culture of Japan and by the fund of Research for the Future Program (JSPS-PFTF96P00206), to which our thanks are due. We also express our appreciation to Toshiba Silicone, Sumitomo Electric Industry, and Tokuyama for financial support.
PY - 1999/9/15
Y1 - 1999/9/15
N2 - The palladium-catalyzed reaction of benzo[1,2:4,5]bis(1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene) (1) with styrene in refluxing benzene afforded two regioisomers of 1:2 adducts, benzo[1,2](1,1,4,4-tetraethyl-2-phenyl-1,4-disilacyclohex-4-ene)[4,5](1,1,4,4- tetraethyl-3-phenyl-1,4-disilacyclohex-4-ene) and benzo[1,2:4,5]bis(1,1,4,4-tetraethyl-2-phenyl-1,4-disilacyclohex-4-ene), whose isomers consist of cis and trans in a ratio of 1:1 in 91% combined yield. Similar reaction of 1 with 1-hexene gave two regioisomers involving cis and trans isomers in 89% combined yield. With ethylene, 1 produced benzo[1,2:4,5]bis(1,1,4,4-tetraethyl-1,4-disilacyclohex-5-ene) (8) in 70% yield, together with a 15% yield of a 2:3 adduct. The platinum-catalyzed reaction of 1 with styrene gave a 1:1 mixture of cis- and trans-benzo[1,2:4,5]bis(2-benzyl-1,1,3,3-tetraethyl-1,3-disilacyclopent-4-ene) in 90% yield. Similar treatment of 1 with 1-hexene produced cis- and trans-benzo[1,2:4,5]bis(1,1,3,3-tetraethyl-2-pentyl-1,3-disilacylopent-4-ene) in a ratio of 1:1 in 92% yield, while with ethylene, 1 afforded 8 as a main product, in addition to two types of 1:2 adduct as minor products.
AB - The palladium-catalyzed reaction of benzo[1,2:4,5]bis(1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene) (1) with styrene in refluxing benzene afforded two regioisomers of 1:2 adducts, benzo[1,2](1,1,4,4-tetraethyl-2-phenyl-1,4-disilacyclohex-4-ene)[4,5](1,1,4,4- tetraethyl-3-phenyl-1,4-disilacyclohex-4-ene) and benzo[1,2:4,5]bis(1,1,4,4-tetraethyl-2-phenyl-1,4-disilacyclohex-4-ene), whose isomers consist of cis and trans in a ratio of 1:1 in 91% combined yield. Similar reaction of 1 with 1-hexene gave two regioisomers involving cis and trans isomers in 89% combined yield. With ethylene, 1 produced benzo[1,2:4,5]bis(1,1,4,4-tetraethyl-1,4-disilacyclohex-5-ene) (8) in 70% yield, together with a 15% yield of a 2:3 adduct. The platinum-catalyzed reaction of 1 with styrene gave a 1:1 mixture of cis- and trans-benzo[1,2:4,5]bis(2-benzyl-1,1,3,3-tetraethyl-1,3-disilacyclopent-4-ene) in 90% yield. Similar treatment of 1 with 1-hexene produced cis- and trans-benzo[1,2:4,5]bis(1,1,3,3-tetraethyl-2-pentyl-1,3-disilacylopent-4-ene) in a ratio of 1:1 in 92% yield, while with ethylene, 1 afforded 8 as a main product, in addition to two types of 1:2 adduct as minor products.
UR - https://www.scopus.com/pages/publications/0011412653
UR - https://www.scopus.com/pages/publications/0011412653#tab=citedBy
U2 - 10.1016/S0022-328X(99)00236-3
DO - 10.1016/S0022-328X(99)00236-3
M3 - Article
AN - SCOPUS:0011412653
SN - 0022-328X
VL - 587
SP - 1
EP - 8
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
IS - 1
ER -