Preparation of 2-alkenylsilanes and 2-alkenylstannanes by the reaction of 2-alkenyl-1,1-cyclopropanedicarboxylate esters with PhMe2SiAlEt2 and (Ph3Sn)2Zn. Generation of 2-alkenyl-3-cyclopentene-1,1-decarboxylates via alkenyl-substituted .PI.-allylpalladiu

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概要

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• Reaction of 2-vinyl-1,1-cyclopropanedicarboxylate with PhMe<SUB>2</SUB>SiAlEt<SUB>2</SUB>, PhMe<SUB>2</SUB>SiZnEt<SUB>2</SUB>Li, or (Ph<SUB>3</SUB>Sn)<SUB>2</SUB>Zn gave 1,7-homoconjugate addition products, 2-alkenylsilanes or 2-alkenylstannanes. In a similar fashion, 2-(1,3-butadienyl)-1,1-cyclopropanedicarboxylate provided the corresponding 1,9-homoconjugate adducts, dienylsilanes or dienylstannanes. The adducts were converted into π-allylpalladium complexes by means of [PdCl<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>2</SUB>]. Treatment of the alkenyl-substituted π-allylpalladium complexes derived from dienylsilanes and [PdCl<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>2</SUB>] with bases such as PPh<SUB>3</SUB> or Na<SUB>2</SUB>CO<SUB>3</SUB> gave 2-alkenyl-3-cyclopentene-1,1-dicarboxylates. In contrast, the reaction of the π-allylpalladiums generated from 2-alkenylsilanes and [PdCl<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>2</SUB>] with the bases resulted in the formation of original vinylcyclopropane derivatives.

• 公益社団法人 日本化学会の論文

著者

• Fugami Keigo

  Department Of Applied Chemistry Faculty Of Engineering Nagasaki University

• Utimoto Kiitiro

  Department Of Industrial Chemistry Faculty Of Engineering Kyoto University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Oshima Koichiro

  Department of Chemistry, Massachusetts Institute of Technology

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