Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 65, Issue 16, Pages 4913-4918Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo000255v
Keywords
-
Categories
Ask authors/readers for more resources
The treatment of aryl-1-alkynes, such as 4-aryl-1-butyne, 5-aryl-1-pentyne, and 6-aryl-1-hexyne, with catalytic amounts of transition metal chlorides, such as PtCl2 and [RuCl2(CO)(3)](2), at 80 degrees C in toluene re suits in cycloisomerization to give dihydronaphthalenes or dihydrobenzocycloheptenes, in which the cyclization mode is dependent on the length of the tethers. The reaction is limited to substrates containing terminal alkynes. A key step of the reaction is the intramolecular interception by an aromatic ring of the vinylmetal complex 2, which contains a cation center at the beta-position, generated from the electrophilic addition of transition metal halides toward an alkyne. The more electron-rich aryl systems are more reactive.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available