Tetrahedron letters

Unique reactivity of a 1, 4-dilithiobutadiene with methyl iodide

PF Hudrlik, D Dai, AM Hudrlik

Index: Hudrlik, Paul F.; Dai, Donghua; Hudrlik, Anne M. Tetrahedron Letters, 2006 , vol. 47, # 20 p. 3427 - 3430

Full Text: HTML

Citation Number: 3

Abstract

Reactions of 1, 4-dilithiobutadiene 5 with MeI in THF gave predominantly methyl iododiene 6. Monolithio monoiodo intermediate 8 was shown not to be involved in the formation of 6, but the results were consistent with the involvement of monolithio monomethyl intermediate 11, which could lead to 6 by metal–halogen exchange. Several other lithioalkenes also reacted with MeI to give alkenyl iodides.

Related Articles:

Regiodivergent Cobalt-Catalyzed Diels–Alder Reactions for the Synthesis of Bifunctional Building Blocks and Their Suzuki-Cross-Coupling Polymerizations

[Hoshi, Takashi; Saitoh, Ippei; Nakazawa, Taichi; Suzuki, Toshio; Sakai, Jun-Ichi; Hagiwara, Hisahiro Journal of Organic Chemistry, 2009 , vol. 74, # 10 p. 4013 - 4016]

Synthesis and catalytic activity of iron complexes with bidentate NHC ligands

[Wu, Jianguo; Dai, Wei; Farnaby, Joy H.; Hazari, Nilay; Le Roy, Jennifer J.; Mereacre, Valeriu; Murugesu, Muralee; Powell, Annie K.; Takase, Michael K. Dalton Transactions, 2013 , vol. 42, # 20 p. 7404 - 7413]

Fe (II)-catalysed homocoupling of arenediazonium tetrafluoroborates

[Zhou, Jiatian; Yu, Shuangshuang; Cheng, Kai; Qi, Chenze Journal of Chemical Research, 2012 , vol. 36, # 11 p. 672 - 674]

Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions

[Journal of the American Chemical Society, , vol. 122, # 17 p. 4020 - 4028]

Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions

[Littke, Adam F.; Dai, Chaoyang; Fu, Gregory C. Journal of the American Chemical Society, 2000 , vol. 122, # 17 p. 4020 - 4028]

More Articles...