-
- Kido Yoshiyuki
- Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
-
- Arisawa Mieko
- Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
-
- Yamaguchi Masahiko
- Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University
この論文をさがす
抄録
GaCl3 promotes addition reactions of carbon nucleophiles to a C-C triple bond. Interaction of alkyne with GaC13 generates a highly reactive electrophile, which aromatic hydrocarbon attacks to give an alkenylated arene. Silylethyne reacts predominantly at the p-position of toluene, while disilylated 1, 3-butadiyne exhibits o-selectivity. The behavior of a silylated 1, 2-propadiene is intermediate between that of the silylethyne and the disilylated 1, 3-butadiyne. In the presence of GaCl3, electrophilic trimerization of silylethyne takes place to give a conjugated hexatriene. In this reaction, silylethyne attacks the GaCl3-activated C-C triple bond. Carbometalation is another interesting addition reaction of an organogallium compound to alkyne. Alkynyldichlorogallium dimerizes in hydrocarbon solvents to give 1, 1-dimetallo-l-buten-3-yne. In the presence of GaCl3, silyl enol ether is ethenylated at the α-carbon atom with trimethylsilylethyne. Treatment of lithium phenoxide with silylethyne in the presence of GaCl3 gives o- (β-silylethenyl) phenol. These reactions involve carbogallation of alkynylgallium, gallium enolate, or gallium phenoxide.
収録刊行物
-
- 有機合成化学協会誌
-
有機合成化学協会誌 58 (11), 1030-1036, 2000
公益社団法人 有機合成化学協会
- Tweet
キーワード
詳細情報 詳細情報について
-
- CRID
- 1390001205278835072
-
- NII論文ID
- 10008821934
-
- NII書誌ID
- AN0024521X
-
- COI
- 1:CAS:528:DC%2BD3cXotFertbs%3D
-
- ISSN
- 18836526
- 00379980
-
- NDL書誌ID
- 5549650
-
- 本文言語コード
- en
-
- データソース種別
-
- JaLC
- NDL
- Crossref
- CiNii Articles
-
- 抄録ライセンスフラグ
- 使用不可