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. 2019 Dec 2;14(23):4223-4228.
doi: 10.1002/asia.201901253. Epub 2019 Oct 23.

Bulky Substituent Effect on Reactivity of Localized Singlet Cyclopentane-1,3-diyls with π-Single Bonding (C-π-C) Character

Rikuo Akisaka  1 , Manabu Abe  1   2   3
Affiliations

Bulky Substituent Effect on Reactivity of Localized Singlet Cyclopentane-1,3-diyls with π-Single Bonding (C-π-C) Character

Rikuo Akisaka et al. Chem Asian J. .

Abstract

Thorough investigation of key intermediates, such as long-lived singlet diradicals, is essential to understand the homolytic bond cleavage reactions. In this study, we evaluate the effect of bulky substituents at the meta-position of the phenyl ring on the bond formation process in singlet 2,2-diethoxy-1,3-diarylcyclopentane-1,3-diyls. The bulky groups have significant influence on the diradical lifetime, as such, when the triisopropylphenyl group was used, the lifetime was 45 times longer than that of the parent diradical in benzene at 293 K.

Keywords: Kinetic stabilization; enthalpy-entropy compensation; laser flash photolysis; singlet diradicals; steric effect.

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