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Issue 7, 2008
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Photochemistry of allyloxybenzophenones: a pseudo-Paternò–Büchi rearrangement accompanied by hydrogen transfer induced 1,5-cyclization

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Abstract

The solution photochemistry of the ortho allyloxy-substituted benzophenone 1 has been investigated in detail. Product analysis revealed formation of a diastereomeric mixture of dihydrobenzofuran derivatives 3 by cyclization via a short-lived intermediate 1,5-biradical and an unusual acetal 4 by a pseudo-Paternò-Büchi rearrangement. The latter reaction pathway was supported by means of laser flash photolysis, where a long-lived intermediate with a maximum absorption band at 380 nm was observed. Besides, theoretical calculations (TD-DFT) of this UV-transient resulted in a band with maximum intensity at 390 nm showing a good correlation between experimental results and theoretical calculations. For comparison, the meta-substituent substrate 2 was also investigated showing preferred triplet–triplet energy transfer.

Graphical abstract: Photochemistry of allyloxybenzophenones: a pseudo-Paternò–Büchi rearrangement accompanied by hydrogen transfer induced 1,5-cyclization

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Publication details

The article was received on 08 May 2008, accepted on 13 May 2008 and first published on 29 May 2008


Article type: Paper
DOI: 10.1039/B807889K
Citation: Photochem. Photobiol. Sci., 2008,7, 782-788
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    Photochemistry of allyloxybenzophenones: a pseudo-Paternò–Büchi rearrangement accompanied by hydrogen transfer induced 1,5-cyclization

    R. Pérez-Ruiz, O. Hinze, Jörg-M. Neudörfl, D. Blunk, H. Görner and A. G. Griesbeck, Photochem. Photobiol. Sci., 2008, 7, 782
    DOI: 10.1039/B807889K

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