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Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: unexpected formation of glycosazones

Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: unexpected formation of glycosazones
Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: unexpected formation of glycosazones
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.
diels-alder reactions, chiral 1, 2-diaza-1, 3-butadienes, cycloadditions, resonance
0022-3263
2378-2381
Avalos, Martin
75b746b8-64d3-4451-be7a-c7c536ed6602
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Clemente, Fernando R.
91b8c77e-79df-4a90-846a-fe0ffec1b090
Gordillo, Ruth
9d99d140-b76f-492b-bb9d-911aed5690fb
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f
Avalos, Martin
75b746b8-64d3-4451-be7a-c7c536ed6602
Babiano, Reyes
b7ffd91c-bacd-4372-ab99-fc30ac2450ae
Cintas, Pedro
29979233-8382-47a8-bde7-1faf4869308c
Clemente, Fernando R.
91b8c77e-79df-4a90-846a-fe0ffec1b090
Gordillo, Ruth
9d99d140-b76f-492b-bb9d-911aed5690fb
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Jiménez, José L.
074cc8fd-9ea1-41fc-b8b6-551d26e5fcd3
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Palacios, Juan C.
2c06e379-89b3-46b1-95c8-7f5057732f9f

Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Clemente, Fernando R., Gordillo, Ruth, Hursthouse, Michael B., Jiménez, José L., Light, Mark E. and Palacios, Juan C. (2002) Novel acid-catalyzed rearrangement of tetrahydro-1,2,3,4-tetrazines: unexpected formation of glycosazones. Journal of Organic Chemistry, 67 (7), 2378-2381. (doi:10.1021/jo0163391 S0022-3263(01)06339-3).

Record type: Article

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.

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More information

Published date: 2002
Keywords: diels-alder reactions, chiral 1, 2-diaza-1, 3-butadienes, cycloadditions, resonance

Identifiers

Local EPrints ID: 39117
URI: http://eprints.soton.ac.uk/id/eprint/39117
ISSN: 0022-3263
PURE UUID: 89fcd406-cb89-451f-9872-4a9d25cf9e4c

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Date deposited: 21 Jun 2006
Last modified: 15 Jul 2019 19:01

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Contributors

Author: Martin Avalos
Author: Reyes Babiano
Author: Pedro Cintas
Author: Fernando R. Clemente
Author: Ruth Gordillo
Author: José L. Jiménez
Author: Mark E. Light
Author: Juan C. Palacios

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