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Photochemical rearrangement reactions of bicyclic molecules that contain a cyclopropane ring

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Abstract

The mechanisms of photochemical rearrangement reactions are studied theoretically using a model system of bicyclic molecules that features a cyclopropane ring that is in proximity to a double bond moiety (such as C[double bond, length as m-dash]C or C [double bond, length as m-dash]O group), using the M06-L method and the 6-311G(d,p) basis set. The theoretical findings show that intersystem crossing is vital to successfully interpret the mechanisms. This theoretical research also shows that the photoisomerization mechanism should proceed as follows: Rea-S0FC-T1Min-T1TS1-T1T1/S0Int1-S0TS2-S0Int2-S0TS3-S0Pro-S0. The theoretical evidence in this work confirms the experimental results for both [3.1.0] and [5.1.0] bicyclic molecules. The theoretical observations also predict that for both [2.1.0] and [4.1.0] systems, the quantum yields of the tautomeric keto forms are greater than those of the corresponding enol isomers.

Graphical abstract: Photochemical rearrangement reactions of bicyclic molecules that contain a cyclopropane ring

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Publication details

The article was received on 13 Apr 2018, accepted on 21 May 2018 and first published on 22 May 2018


Article type: Paper
DOI: 10.1039/C8NJ01795F
Citation: New J. Chem., 2018, Advance Article
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    Photochemical rearrangement reactions of bicyclic molecules that contain a cyclopropane ring

    S. Su and M. Su, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ01795F

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