Tetrahedron

Synthetic scope, computational chemistry and mechanism of a base induced 5-endo cyclization of benzyl alkynyl sulfides

…, Á Castillo, A Greer, LK Montemayer, EE Sheepwash…

文献索引：Motto, John M.; Castillo, Alvaro; Greer, Alexander; Montemayer, Laura K.; Sheepwash, Erin E.; Schwan, Adrian L. Tetrahedron, 2011 , vol. 67, # 5 p. 1002 - 1010

全文：HTML全文

被引用次数: 19

摘要

We present an experimental and computational study of the reaction of aryl substituted benzyl 1-alkynyl sulfides with potassium alkoxide in acetonitrile, which produces 2-aryl 2, 3- dihydrothiophenes in poor to good yields. The cyclization is most efficient with electron withdrawing groups on the aromatic ring. Evidence indicates there is rapid exchange of protons and tautomerism of the alkynyl unit prior to cyclization. Theoretical calculations ...