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Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles

Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles
Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles
The oxidation of 3-[bis-(diaryl)methyl]chromones 2 with p-chloranil affords novel acetals, 3-[bis-(diaryl)methylene]-2-methoxychroman-4-ones, 4 through interception of a pyrylium type intermediate. Oxidation of 3-(2-hydroxyphenyl)-4-[bis-(diaryl)methyl]pyrazoles 8, derived from 2 and hydrazines, gave 4,4-diarylbenzopyrano[4,3-c]pyrazoles 15. The electronic absorption spectra of 4 and 15 upon protonation are comparable with those of triarylmethine cationic dyes.
photochromic properties, derivatives, 3-formylchromone, condensation, chromones, spectra, route
0040-4020
10945-10953
Gabbutt, Christopher D.
d57acd39-7728-473a-81c6-82dfc71a30da
Hargrove, Tessa F.L.
c3b6ae4f-3d88-409d-878d-df95a56e4c8b
Heron, B. Mark
2f65af97-0fdc-40e5-904d-5db8765b2e82
Jones, David
83788d9d-a76c-41e1-b824-5c55bb2eef3d
Poyner, Carley
400b742c-5a96-4e21-8b0d-0d96a30d744a
Yildiz, Emel
c982115d-05d7-40fa-bb7d-368a88c7c35e
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Gabbutt, Christopher D.
d57acd39-7728-473a-81c6-82dfc71a30da
Hargrove, Tessa F.L.
c3b6ae4f-3d88-409d-878d-df95a56e4c8b
Heron, B. Mark
2f65af97-0fdc-40e5-904d-5db8765b2e82
Jones, David
83788d9d-a76c-41e1-b824-5c55bb2eef3d
Poyner, Carley
400b742c-5a96-4e21-8b0d-0d96a30d744a
Yildiz, Emel
c982115d-05d7-40fa-bb7d-368a88c7c35e
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Gabbutt, Christopher D., Hargrove, Tessa F.L., Heron, B. Mark, Jones, David, Poyner, Carley, Yildiz, Emel, Horton, Peter N. and Hursthouse, Michael B. (2006) Oxidation and ring cleavage reactions of 3-benzhydrylchromones. Generation of triarylmethine cations from methylidenechroman-4-ones and benzopyrano[4,3-c]pyrazoles. Tetrahedron, 62 (47), 10945-10953. (doi:10.1016/j.tet.2006.08.090).

Record type: Article

Abstract

The oxidation of 3-[bis-(diaryl)methyl]chromones 2 with p-chloranil affords novel acetals, 3-[bis-(diaryl)methylene]-2-methoxychroman-4-ones, 4 through interception of a pyrylium type intermediate. Oxidation of 3-(2-hydroxyphenyl)-4-[bis-(diaryl)methyl]pyrazoles 8, derived from 2 and hydrazines, gave 4,4-diarylbenzopyrano[4,3-c]pyrazoles 15. The electronic absorption spectra of 4 and 15 upon protonation are comparable with those of triarylmethine cationic dyes.

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More information

Published date: 2006
Keywords: photochromic properties, derivatives, 3-formylchromone, condensation, chromones, spectra, route

Identifiers

Local EPrints ID: 44444
URI: http://eprints.soton.ac.uk/id/eprint/44444
ISSN: 0040-4020
PURE UUID: d5fc1919-c199-4dda-b434-aad39382f68c
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

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Date deposited: 28 Feb 2007
Last modified: 20 Jul 2019 01:08

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Contributors

Author: Christopher D. Gabbutt
Author: Tessa F.L. Hargrove
Author: B. Mark Heron
Author: David Jones
Author: Carley Poyner
Author: Emel Yildiz
Author: Peter N. Horton ORCID iD

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