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Derives de l'imidazothiazole. V. Transposition allylique observee au cours de la synthese d'(imino-2 alkyl-3 thiazolinyl-4) acetates d'ethyle et de (dihydro-5,6 imidazothiazolyl-3) acetates d'ethyle
Robert, Jean-Francois,Panouse, Jacques J.
, p. 343 - 348 (2007/10/02)
Ethyl (6-phenyl-5,6-dihydroimidazothiazol-3-yl) acetate hydrobromide shows an allylic transposition in alkaline medium and gives ethyl (6-phenyl-2,3,5,6-tetrahydroimidazothiazol-3-ylidene)acetate.This compound possesses an exocyclic double bond which is stable upon acidification.The intermediate ethyl (2-imino-3-alkylthiazolin-4-yl)acetates undergo an analogous transposition upon treatment with base, which is reversible upon acidification.These transpositions were observed in the pmr data.The steric constraint and ? p ? conjugation are discussed in this work.
