Tetrahedron

Reactions of some alkynyl halides with Samarium (II) iodide

Z Zhou, D Larouche, SM Bennett

文献索引：Zhou, Zhihong; Larouche, Denis; Bennett, Sharon M. Tetrahedron, 1995 , vol. 51, # 43 p. 11623 - 11644

被引用次数: 34

摘要

Certain alkynyl halides (6-halo-1-ynes) react with samarium (II) iodide (SmI2) to give cyclized products (methylenecyclopentanes) in good yield. We have found some interesting evidence for the presence of radical and unstable organosamarium intermediates in these reductive cyclizations. Methyl 7-halohept-2-ynoates are not. however, good substrates for this cyclization methodology.

~79%

~80%

~0%

~39%

详细

~1%

~0%

详细

Catalytic reduction and intramolecular cyclization of haloal...

[Ischay, Michael A.; Mubarak, Muhammad S.; Peters, Dennis G. Journal of Organic Chemistry, 2006 , vol. 71, # 2 p. 623 - 628]

Electrochemical reduction of 1-iodo-5-decyne and 1-bromo-5-d...

[Shao, Rui-lian; Cleary, James A.; Perriere, Daniel M. La; Peters, Dennis G. Journal of Organic Chemistry, 1983 , vol. 48, # 19 p. 3289 - 3294]

Cyclization of acetylenic alkyllithiums

[Bailey, William F.; Ovaska, Timo V. Journal of the American Chemical Society, 1993 , vol. 115, # 8 p. 3080 - 3090]

Cyclizations during the Grignard Reactions of co-Bromoalkyne...

[Crandall, Jack K.; Michaely, William J.; Collonges, Francois; Nelson, Deanna J.; Ayers, Timothy A.; Gajewski, Joseph J. Croatica Chemica Acta, 1996 , vol. 69, # 4 p. 1473 - 1490]