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  Photochemical dehydrogenation, ring contraction, and ring expansion of hydrogenated derivatives of benzoxazino-benzoxazine, quinoxalino-quinoxaline, and bibenzothiazole.

Tauer, E., & Grellmann, K. H. (1990). Photochemical dehydrogenation, ring contraction, and ring expansion of hydrogenated derivatives of benzoxazino-benzoxazine, quinoxalino-quinoxaline, and bibenzothiazole. Chemische Berichte, 123(5), 1149-1154. doi:10.1002/cber.19901230531.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0013-0DEA-C Version Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-301D-5
Genre: Journal Article

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 Creators:
Tauer, E.1, Author              
Grellmann, K. H.1, Author              
Affiliations:
1Department of Spectroscopy and Photochemical Kinetics, MPI for biophysical chemistry, Max Planck Society, ou_578624              

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 Abstract: The photochemical properties of the title compounds have been investigated and compared. The benzoxazino-benzoxazine derivatives 1 are photochemically converted into hydrogenated oxazole derivatives. In some cases this ring contraction is accompanied by a dehydrogenation reaction whereby the heterocyclic ring system becomes aromatic. Hydrogenated quinoxalino-quinoxalines also undergo a photodehydrogenation reaction and become aromatic. However, a ring contraction yielding the imidazolyl system does not take place. The only investigated sulfur-containing analog has different properties. The stable form is the bibenzothiazole 23 which contains a five-membered heterocyclic ring system. Photochemically 23 rearranges under ring expansion to give the benzothiazino-benzothiazine 24.

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Language(s): eng - English
 Dates: 1990-05
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1002/cber.19901230531
ISI: A1990DF41500030
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Title: Chemische Berichte
Source Genre: Journal
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Pages: - Volume / Issue: 123 (5) Sequence Number: - Start / End Page: 1149 - 1154 Identifier: ISSN: 0009-2940