Formation of exceptionally stable ketene during photo transformations of Bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores

Submitting author affiliation:
Hooghly Mohsin College, Chinsurah, Hooghly, West Bengal, Hooghly, India

Beilstein Arch. 2019, 201979.

Published 30 Jul 2019

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Photoreaction of Bicyclo[2.2.2]oct-5-en-2-ones having mixed chromophores like 5,6 dibenzoyl moiety and phenyl or isopropenyl like electron withdrawing groups at the bridgehead position have been checked in different solvent and different wavelength. In all cases regioselective 1,5-photophenyl migration leading to vinyl ketenes from more congested site of the molecule to the less one have been observed. The ketenes were exceptionally stable both in air and in solution. Its stability studies in acetonitrile through time dependent UV absorbance spectra revealed that it remained almost unchanged at least for couple of weeks. 

Keywords: Bridgehead position; enones; ketene; mixed chromophores

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Ghosh, A. Beilstein Arch. 2019, 201979. doi:10.3762/bxiv.2019.79.v1

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