Papers

Oct, 2002

Platinum complex-catalyzed hydrosilylation and isomerization of methylenecyclopropane derivatives. Effect of structures of the substrate and catalyst

JOURNAL OF ORGANIC CHEMISTRY
  • M Itazaki
  • ,
  • Y Nishihara
  • ,
  • K Osakada

Volume
67
Number
20
First page
6889
Last page
6895
Language
English
Publishing type
Research paper (scientific journal)
DOI
10.1021/jo020293+
Publisher
AMER CHEMICAL SOC

PtI2(PPh3)(2) catalyzes hydrosilylation of 2,2-diphenyl-1-methylenecyclopropane with HSiEt3, HSiPh3, HSiEt2Ph, HSiPhCl2, and HSiCl3 under solvent-free conditions at 140 degreesC to produce the silyl compounds with a (2,2-diphenyleyclopropyl)methyl substituent in moderate to high yields without ring-opening of the substrate. PtI2(PPh3)(2) is converted by the reaction into PtH(I)(PPh3)(2), which also catalyzes the hydrosilylation of the methylenecyclopropanes. The reaction of 2-phenyl-1-methylenecyclopropane, 2-methyl-2-phenyl-1-methylenecyclopropane, 2,2-diphenethyl-1-methyl-enecyclopropane, and alkylidenecyclopropanes with HSiEt3 catalyzed by PtI2(PPh3)(2) causes addition of hydrosilane to the substrate accompanied by ring-opening. 2,2-Diphenyl-1-methylenecyclopropane undergoes ring-opening isomerization in the presence of HSi(OEt)Me-2 and Pt(PEt3)(3) catalyst to give 1,1-diphenyl-1,3-butadiene. The pathways for the hydrosilylation and the isomerization are discussed.

Link information
DOI
https://doi.org/10.1021/jo020293+
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000178381600005&DestApp=WOS_CPL
ID information
  • DOI : 10.1021/jo020293+
  • ISSN : 0022-3263
  • Web of Science ID : WOS:000178381600005

Export
BibTeX RIS