N. N. Volkova, E. V. Tarasov, M. I. Kodess, W. Dehaen, V. A. Bakulev, “Ring opening in di[1,2,3]triazolo-[1,3,6]thiadiazepine and -[3,1,5]benzothiadiazepine in reactions with butyllithium”, Mendeleev Commun., 2002, Volume 12, Issue 4,Pages <nobr>131

This article is cited in 7 papers

Ring opening in di[1,2,3]triazolo-[1,3,6]thiadiazepine and -[3,1,5]benzothiadiazepine in reactions with butyllithium

N. N. Volkova^a, E. V. Tarasov^a, M. I. Kodess^b, W. Dehaen^c, V. A. Bakulev^a

^a Department of Technology of Organic Synthesis, Urals State Technical University, Ekaterinburg, Russian Federation
^b I. Ya. Postovsky Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^c Department of Chemistry, University of Leuven, Leuven, Belgium

Abstract: Di[1,2,3]triazolo[1,5-a:5’,1’-d][3,1,5]benzothiadiazepine treated with butyllithium undergoes ring opening via the thiophilic addition of butyllithium at the C–S bond, whereas 9,10-dihydrodi[1,2,3]triazolo[1,5-b:5’,1’-f][1,3,6]thiadiazepine mainly undergoes lithiation of the methylene group followed by C–N bond cleavage to give 1-vinyltriazolyl sulfide.

Language: English

DOI: 10.1070/MC2002v012n04ABEH001625