Photochemistry of the carbon‐nitrogen double bond

Wettermark, Gunnar

doi:10.1002/9780470771204.ch12

Cited by 18 publications

(19 citation statements)

References 99 publications

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“…21 The Koch group disclosed their work in pursuit of azetidines through [2 + 2] cycloadditions in 1972. Initial efforts focused on the ability of 3ethoxyisoindolone (15) to undergo aza Paternò-Büchi reactions with a variety of sterically and electronically differentiated alkenes under UV light irradiation (Fig. 8).…”

Section: Scope and Limitationsmentioning

confidence: 99%

“…For example, benzophenone imine absorbs strongly at 260 nm, likely due to a π–π* transition, while a weaker absorption at 340 nm is attributed to a n–π* transition. 15 , 16 The specific excited states participating in aza Paternò–Büchi reactions have only been reported for a limited number of substrates. For example, Koch suggested that the excited state reactions of keto imino ethers occur from low-energy π–π* states, while unreactive compounds possess low-energy n–π* states.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

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Synthesis of azetidines by aza Paternò–Büchi reactions

2020

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Section: Scope and Limitationsmentioning

confidence: 99%

Section: Mechanistic Considerationsmentioning

confidence: 99%

Synthesis of azetidines by aza Paternò–Büchi reactions

2020

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“…We have previously reported our observations8*' on the photochemical reactivity of the imines (4) derived from the aldehyde (5). All of these were photochemically reactive to some extent and rearranged to (6) by way of the aza-di-lr-methane process, a reaction route which has seldom been observed.…”

Section: Ar-+numentioning

confidence: 99%

Studies on the scope of the aza-di-π-methane rearrangement of β,γ-unsaturated imines

Armesto¹,

Langa²,

Martin³

et al. 1987

J. Chem. Soc., Perkin Trans. 1

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The syntheses of i mi nes of 2,2,4,4tetra p hen yl but -3ena I, 3,3 -d imet hyl -5 5dip henyl pent -4 -en -2 -one, and 2,2-dimethyl-l,4,4-triphenylbut-3-en-l -one are described. The results of the irradiation of these and of 2,2-dimethyl-4,4-diphenylbut-3-enonitrile and 2,2-dimethyl-4,4-diphenylbut-3-enal oxime are discussed. The N-isopropyl imine of 2,2,4,4-tetraphenylbut-3-enal and the N-phenyl and benzyl imines of 3,3-dimethyl-5,5-diphenylpent-4-en-2-one undergo the 1 -aza-di-n-methane rearrangement.

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“…consistent with the presence of -HC=N-groups. Moreover, cyclic imines or pyrazines might be expected to promote further formation of 8 by either photoinduced electron transfer or hydrogen abstraction (Wettermark, 1970).…”

Section: Discussionmentioning

confidence: 99%

The Photochemistry of Piperazine‐2,5‐dione in Aqueous Solution

Coyle

Hill

Randall³

1984

Photochem & Photobiology

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The aqueous photochemistry of deoxygenated solutions of piperazine‐2,5‐dione was investigated and three products were isolated in low yield using preparative high‐performance liquid chromatography: 3,3′‐bis(piperazine‐2,5‐dione) (1), oxamide and N‐methyloxamide. The structure of 1 was established by infrared, mass and high‐field proton magnetic resonance spectroscopy, and by the synthesis of its meso diastereoisomer. A 1:2 mixture of meso and racemic diastereoisomers of 1 was formed in good yield in thermally or photochemically initiated reactions of piperazine‐2,5‐dione with t‐butyl peroxide in aqueous t‐butanol. The rate of photolysis of aqueous piperazine‐2,5‐dione was markedly enhanced in the presence of iron(II) ions, copper(II) ions or powdered titanium dioxide. A diastereomeric mixture of 1, oxamide and N‐methyloxamide were isolated from the reaction with iron(II) ions. The possibility that oxamides were formed in these reactions via reaction with atmospheric oxygen was eliminated in a series of control experiments. The results suggest α‐carbon radicals are important in the photolysis of peptides in fluid aqueous media, possibly as a consequence of photoinduced electron transfer. No significant adduct formation could be detected when mixtures of piperazine‐2,5‐dione and uracil or thymine were irradiated in frozen aqueous solution.

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Photochemistry of the carbon‐nitrogen double bond

Cited by 18 publications

References 99 publications

Synthesis of azetidines by aza Paternò–Büchi reactions

Synthesis of azetidines by aza Paternò–Büchi reactions

Studies on the scope of the aza-di-π-methane rearrangement of β,γ-unsaturated imines

The Photochemistry of Piperazine‐2,5‐dione in Aqueous Solution

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