Tetrahedron

Diels–Alder reactions of perfluoroketene dithioacetals with electron-rich 1, 3-dienes: a new access to polysubstituted aromatic sulfides

JP Bouillon, S Mykhaylychenko, S Melissen, A Martinez…

Index: Bouillon, Jean-Philippe; Mykhaylychenko, Sergiy; Melissen, Sigismund; Martinez, Agathe; Harakat, Dominique; Shermolovich, Yuriy G. Tetrahedron, 2012 , vol. 68, # 41 p. 8663 - 8669

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Citation Number: 4

Abstract

The present paper describes the Diels–Alder reactions of perfluoroketene dithioacetals with electron-rich 1, 3-dienes (2, 3-dimethylbuta-1, 3-diene, isoprene, penta-1, 3-diene) followed by spontaneous HF and thiol elimination, leading to polysubstituted aromatic sulfides in moderate to good yields. Reactions seem to be dependent on the substitution patterns of perfluoroketene dithioacetals; the best results were obtained from trifluoromethyl or ...