title: Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: unexpected formation of glycosazones.
abstract: The present contribution discloses a simple and unexpected acid-catalyzed cleavage of tetrahydrotetrazines leading to 1,2-bis(hydrazones). Incorporation of a chiral fragment derived from carbohydrates enables the rapid preparation of glycosazones, a family of compounds employed by Emil Fischer to elucidate the configuration of sugars. In addition, a mechanistic proposal accounts for experimental observations.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura, E-06071 Badajoz, Spain.
authors.forename: Martín
authors.initials: M
authors.lastname: Avalos
authors.forename: Reyes
authors.initials: R
authors.lastname: Babiano
authors.forename: Pedro
authors.initials: P
authors.lastname: Cintas
authors.forename: Fernando R
authors.initials: FR
authors.lastname: Clemente
authors.forename: Ruth
authors.initials: R
authors.lastname: Gordillo
authors.forename: Michael B
authors.initials: MB
authors.lastname: Hursthouse
authors.forename: José L
authors.initials: JL
authors.lastname: Jiménez
authors.forename: Mark E
authors.initials: ME
authors.lastname: Light
authors.forename: Juan C
authors.initials: JC
authors.lastname: Palacios