Radical anionic cyclization reactions via photochemically induced electron transfer

Bischof, Eric W.; Mattay, Jochen

doi:10.1016/s0040-4039(00)97261-7

Cited by 23 publications

(2 citation statements)

References 9 publications

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“…Recently it has been shown that radical anionic cyclization of olefinic enones effectively compete with intramolecular [2 + 2]-cycloaddition to form spirocyclic compounds [205,206]. 3-Alkenyloxy-and 3-alkenyl-2-cyclohexenones 235 are irradiated in the presence of triethylamine.…”

Section: Radical Anions Of Afl-unsaturated Carbonyi Compoundsmentioning

confidence: 99%

Radical ion cyclizations

Hintz

Heidbreder

Mattay

1996

Electron Transfer II

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Section: Radical Anions Of Afl-unsaturated Carbonyi Compoundsmentioning

confidence: 99%

Radical ion cyclizations

Hintz

Heidbreder

Mattay

1996

Electron Transfer II

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“…An alkyne‐carbonyl cyclization reaction, for example, was used to prepare bicyclic tertiary cycloalkanols by photoreductively induced electron transfer from triethylamine (TEA) as a strong reducing agent in acetonitrile or by photoionization in pure hexamethylphosphoric triamide (HMPA) 28,29. Furthermore, one of the first examples of a PET‐induced cleavage of a cyclobutane ring focused on organic synthesis was reported by Bischof and Mattay 30. The most recent examples involved reductive PET reactions between α‐cyclopropyl ketones and TEA as electron source and/or lithium perchlorate (LiClO 4 ) as additive to provide the ketyl radical anion and the corresponding donor radical cation 24–27, 31.…”

Section: Introductionmentioning

confidence: 99%

Photoreactions of Tricyclic α‐Cyclopropyl Ketones and Unsaturated Enones – Synthesis of Polyquinanes and Analogous Ring Systems

Tzvetkov¹,

Neumann²,

Stammler³

et al. 2006

Eur J Org Chem

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Polycyclic systems of both angular and propellane type have been synthesized through intramolecular radical cyclization reactions, by photochemically induced electron transfer of tricyclic α‐cyclopropyl ketones or by photolysis of unsaturated enones. In general, tricyclic α‐cyclopropyl ketones, each bearing an alkynyl or alkenyl side chain at the position γ to the carbonyl group, were used as starting materials. The reactions resulted in regioselective cleavage of one cyclopropyl bond with formation of tri‐ to tetracyclic ring systems by a tandem fragmentation‐radical/radical anionic reaction pathway. The regioselectivity of the cyclization (exo/endo) depends on the length of the unsaturated side chain. In cases involving α‐cyclopropane derivatives with alkoxymethyl side chains, various non‐cyclization processes were observed. In addition, the photoinduced cyclization of the corresponding bicyclic enone derivatives with the same unsaturated side chains afforded tetra‐ and tricyclic products of propellane type in good yields and with high stereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Electron‐transfer Reactions of Amines

Das¹,

Suresh²

2001

Electron Transfer in Chemistry

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Radical anionic cyclization reactions via photochemically induced electron transfer

Cited by 23 publications

References 9 publications

Radical ion cyclizations

Radical ion cyclizations

Photoreactions of Tricyclic α‐Cyclopropyl Ketones and Unsaturated Enones – Synthesis of Polyquinanes and Analogous Ring Systems

Electron‐transfer Reactions of Amines

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