Journal of Organic Chemistry p. 4482 - 4486 (1984)
Update date:2022-08-02
Topics:
Albertazzi, A.
Leardini, R.
Pedulli, G.F.
Tundo, A.
Zanardi, G.
The reaction of 6-X-1,2,3-benzothiadiazoles (1) with the radicophilic alkenes 1,1-diphenylethylene (2) and 1-cyano-1-(tert-butylthio)ethylene (3) and the alkynes PhC<*>CR (4, R=H or Ph) in di-tert-butyl peroxide (TBP) leads to the cycloadducts 5, 7, and 8.The proposed mechanism involves an initial attack by tert-butoxy radical at the sulfur atom of 1 affording the radical intermediate 9 which is responsible for the formation of all the reaction products.
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