Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 3, Pages 731-735Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo020406p
Keywords
-
Categories
Ask authors/readers for more resources
The [4 + 2]-cycloaddition reaction of 1-phenyl-1-benzothiophenium triflates has been conducted for the first time. [4 + 2]-Cycloaddition with dienes such as cyclopentadiene and 1,3-diphenyl-isobenzofuran occurs successfully to give cycloadducts. This result indicates that the C=C bond of the thiophene ring acts as a 2pi electron component in the cycloaddition reaction. Cycloadducts were formed in high yields with high stereoselectivity. However, the cycloaddition with other less reactive dienes such as 2,3-dimethyl-1,3-butadiene did not take place. The structure and stereochemistry of cycloadduct 2a were analyzed by NMR techniques. Furthermore, reaction of the cycloadducts with sodium methoxide in methanol gave the ring-opened products in high yields.
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