Hydroxyallylpyridyl derivatives exhibited a peculiar thermal behavior likely ascribed to the weak acidity of the picolinetype hydrogen atom on the C-1 carbon of the allyl residue, leading to allyl inversion products. The unprotected alcohol reacted as vinylogous picoline carbon nucleophile with stronglyactivated heterocyclic counterparts. A mechanistic rationale for this unprecedented reactivitywas proposed.
New reactivity of hydroxyallylpyridyl derivatives as C-3 carbon nucleophiles / D. Giomi; M. Piacenti; A. Brandi. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 45:(2004), pp. 2113-2115. [10.1016/j.tetlet.2004.01.049]
New reactivity of hydroxyallylpyridyl derivatives as C-3 carbon nucleophiles
GIOMI, DONATELLA;BRANDI, ALBERTO
2004
Abstract
Hydroxyallylpyridyl derivatives exhibited a peculiar thermal behavior likely ascribed to the weak acidity of the picolinetype hydrogen atom on the C-1 carbon of the allyl residue, leading to allyl inversion products. The unprotected alcohol reacted as vinylogous picoline carbon nucleophile with stronglyactivated heterocyclic counterparts. A mechanistic rationale for this unprecedented reactivitywas proposed.File | Dimensione | Formato | |
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