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

Gabbutt, Christopher D.; Hargrove, Tessa F.L.; Heron, B. Mark; Jones, David; Poyner, Carley; Yildiz, Emel; Horton, Peter N.; Hursthouse, Michael B.

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

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). pp. 10945-10953. ISSN 0040-4020

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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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URI:

https://eprints.hud.ac.uk/id/eprint/15075

Title:

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

Creators:

Gabbutt, Christopher D., Hargrove, Tessa F.L., Heron, B. Mark, Jones, David, Poyner, Carley, Yildiz, Emel, Horton, Peter N. and Hursthouse, Michael B.

Identification Number:

10.1016/j.tet.2006.08.090

Official URL:

http://dx.doi.org/10.1016/j.tet.2006.08.090

Date:

November 2006

Subjects:

Q Science > Q Science (General)
Q Science > QD Chemistry

Schools:

School of Applied Sciences

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