Theoretical Study on the Reactivity and Regioselectivity of the Ene Reaction of  1 Δ g  O 2  with α,β‐Unsaturated Carbonyl Compounds | Zendy

Maranzana Andrea | Zendy; Canepa Carlo | Zendy; Ghigo Giovanni | Zendy; Tonachini Glauco | Zendy

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Theoretical Study on the Reactivity and Regioselectivity of the Ene Reaction of 1 Δ g O 2 with α,β‐Unsaturated Carbonyl Compounds

Author(s) -

Maranzana Andrea,

Canepa Carlo,

Ghigo Giovanni,

Tonachini Glauco

Publication year - 2005

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500215

Subject(s) - chemistry , regioselectivity , ene reaction , diradical , dioxetane , singlet oxygen , singlet state , reactivity (psychology) , photochemistry , reaction mechanism , transition state , solvent , medicinal chemistry , solvent effects , computational chemistry , oxygen , organic chemistry , catalysis , excited state , medicine , alternative medicine , pathology , physics , chemiluminescence , nuclear physics

The ene reaction of singlet oxygen with α,β‐unsaturated carbonyl compounds gives unsaturated hydroperoxides and displays interesting features: Different reactivities of the s ‐ cis and s ‐ trans reactants and a marked regioselectivity, influenced to some extent by solvent polarity. All of these traits are accounted for by a polar diradical mechanism. A perepoxide intermediate is not a critical point on the reaction’s potential energy surface. Also, a trioxene intermediate is located too high in energy to be significantly populated. An alternative pathway leading to dioxetane is not as effective as the ene pathway giving the hydroperoxide. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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