Darstellung und Reaktionen von 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2 H-isoindolen/ Preparation and Reactions of 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2H-isoindoles

Troll, T.; Schmid, Klaus; Rasch, Ingrid

doi:10.1515/znb-1987-0817

Cited by 5 publications

(1 citation statement)

References 2 publications

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“…Only a few of cyclic voltammetric peak potentials for the electroreduction (ER) of selected O ‐acyl derivatives of NHPI in acetonitrile and the polarographic half‐wave potentials in methanol are known. One can also mention ER of benzyloxyphthalimide in aprotic medium in the presence of chlorotrimethylsilane that led to silylation of the substrate …”

Section: Introductionmentioning

confidence: 99%

Electrochemical behavior of N‐oxyphthalimides: Cascades initiating self‐sustaining catalytic reductive N―O bond cleavage

Syroeshkin

Krylov

Hughes

et al. 2017

J of Physical Organic Chem

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N-oxyphthalimides are stable and easily accessible compounds that can produce oxygen radicals upon 1-electron reduction. We present a systematic study of electrochemical properties of N-oxyphthalimide derivatives (PI-ORs) in DMF by cyclic voltammetry. In all cases, electron transfer to the substrate leads to decomposition of the intermediate radical anion via the N-O bond cleavage. In the case of benzyloxyphthalimide or its derivatives containing electrondonating substituents, reductive electron transfer induces the chain decomposition of the substrate to phthalimide (PI) radical-anion and the corresponding carbonyl compound. The PI radical-anion product is a powerful reductant that can transfer an electron to the reactant PI-OR, thus establishing a catalytic cycle for reductive N-O scission. This self-catalytic process is reflected in a considerable decrease in the reduction current for the substrate (<1e -/molecule). By contrast, reductive fragmentations of benzyl derivatives containing electronwithdrawing substituents in the aromatic ring or at the benzylic position, as well as tosyl and alkyl derivatives, occur via a 1-electron mechanism. A sequence of N-O and C-C scissions was engineered to support the intermediacy of O-centered radicals in these processes.

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Section: Introductionmentioning

confidence: 99%

Electrochemical behavior of N‐oxyphthalimides: Cascades initiating self‐sustaining catalytic reductive N―O bond cleavage

Syroeshkin

Krylov

Hughes

et al. 2017

J of Physical Organic Chem

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Oxo(tri‐ tert ‐butylphenyl)boran ArBO als Zwischenstufe

Groteklaes

Paetzold

1988

Chem. Ber.

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O x~t r i -t e r t -b u t y l p y l )~~~ ArB E 0 as an IntermediateThe borane ArB(0Me)z (1) (Ar = 2,4,6-tri-tert-butylphenyl) was transformed into ArBH3 . Li(tmeda) (2) by the action of LiAIH, in Et20. The product 2 can be hydrolysed to ArB(0H)H (3), but in strongly acidic media the hydrolysis involves the attack of a neighbouring methyl group to give the l-hydroxy-l-boraindane derivative 4. Borane 3 can be dehydrogenated to 4 in the gas-phase at 600°C. AuDer dem oben erwlhnten Bericht iiber zwei Abfangversuche von 5" sind uns bisher an experimentellen Daten iiber Organyl-(oxo)borane RBO nur das M a s s e n s p e k t r~m~~~' und das Photoelektronenspektrum von MeB06' bekannt. Ahnlich wie bei den verwandten Iminoboranen vom Typ RB = NR"' diirfte auch bei den Oxoboranen eine Valenzstrichformel RB = 0 rnit einer BO-Dreifachbindung den wirklichen Bindungsverhiltnissen nahekommen, ohne daD der negativen Formalladung am Bor und der positiven Formalladung am Sauerstoff in einer solchen Formel reale Bedeutung zukime. Diese Anschauung wird fur MeBO durch eine Abintio-Rechnung rnit einer 4-31G-Basis gestiitzt 81.

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Umlagerung und Abbau bicyclischer Amin—Tetraorganodiboroxane^[1]

et al. 1994

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Rearrangement and Degradation of Bicyclic Amine-Tetraalkyldiboroxanes[llThe amine-tetraalkyldiboroxanes C ( R ' , R 7 ' ) B ( R 1 ) O m give the unsaturated rac-amino-trialkyldiboroxane MezN-(R4)CHz$JMez [ l a : R1r4,?r7' = Et; l b : R1t4s7 = Et, R7' = Ph; lb': B ( E t ) 0 m * ( E t ) C ( E t ) = C H 2 (rac-3) (X-ray structure anaR4a7r7' = Et, R' = Ph; l c : R1m7>?' = Et, R4 = Ph] react on heating lysis) by intramolecular 1,2-deaminoboration. rac-3 is characby EtBO elimination and allylborane rearrangement to yield terized by reaction with (EtzBH)2 and (Et2BD), with formation the allyl-aminoboranes Me2NB(Et)CH2C(R4) =C(R7r7') [2a: of the 1,2,6-oxadiborinane 5 by evolution of Hz or HD respec-

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Darstellung und Reaktionen von 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2 H-isoindolen/ Preparation and Reactions of 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2H-isoindoles

Cited by 5 publications

References 2 publications

Electrochemical behavior of N‐oxyphthalimides: Cascades initiating self‐sustaining catalytic reductive N―O bond cleavage

Electrochemical behavior of N‐oxyphthalimides: Cascades initiating self‐sustaining catalytic reductive N―O bond cleavage

Oxo(tri‐ tert ‐butylphenyl)boran ArBO als Zwischenstufe

Umlagerung und Abbau bicyclischer Amin—Tetraorganodiboroxane^[1]

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Darstellung und Reaktionen von 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2 H-isoindolen/ Preparation and Reactions of 2-Alkoxy-1,3-bis-(trimethylsilyloxy)-2H-isoindoles

Cited by 5 publications

References 2 publications

Electrochemical behavior of N‐oxyphthalimides: Cascades initiating self‐sustaining catalytic reductive N―O bond cleavage

Electrochemical behavior of N‐oxyphthalimides: Cascades initiating self‐sustaining catalytic reductive N―O bond cleavage

Oxo(tri‐ tert ‐butylphenyl)boran ArBO als Zwischenstufe

Umlagerung und Abbau bicyclischer Amin—Tetraorganodiboroxane[1]

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Umlagerung und Abbau bicyclischer Amin—Tetraorganodiboroxane^[1]