C-nitroso compounds. Part V. The preparation of cis-azodioxy compounds (cis-dimeric nitroso compounds)

Mackor, A.; Wajer, Th. A. J. W.; Boer, Th. J. de

doi:10.1016/s0040-4039(00)90853-0

Cited by 17 publications

(10 citation statements)

References 9 publications

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“…Since our source of C-nitroso compounds were dimers, throughout this report irradiation was carried out in a Pyrex apparatus (energy cut-off <290 nm) so that both dimer and monomer absorption bands were excited; the former excitation promoted the dissociation of dimers 2 or 3 to the corresponding monomer (10).…”

Section: Photodecompositionmentioning

confidence: 99%

“…Owing to precipitation of the syn-isomer the photolysis required a prolonged irradiation for completion. From these photolyses trans-I-nitrato-2-chlorocyc1ohexane (10) and trans-1-nitro-2-chlorocyclohexane (12) were isolated by column chromatography. The corresponding cis-isomer of 12 was not detected in the photolysate in spite of careful chromatog- cis-isomer of nitrate 10 is suggested by the v.p.c.…”

Section: Photodecompositionmentioning

confidence: 99%

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Photoreactions of Nitroso Compounds in Solution. XXIV. Photooxidation and Photodecomposition of C-Nitroso Compounds

Chow¹,

Tam²,

Pillay³

1973

Can. J. Chem.

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Irradiation of the anti-dimers of C-nitroso compounds under nitrogen caused dissociation to the corresponding C-nitroso monomer which underwent photodisproportionation. tautomerization, and dimerization. Similar irradiation underhoxygen led principally to nitrate and nitrc~ compound formation. The disproportionation of N-(4-nitrosohexyl)acetamide was shown to occur by photodissociation of the C-nitroso monomer to the alkyl radical and nitric oxide. Under an oxygen atmosphere, those C-nitroso compounds which could undergo facile photodissociation were quickly oxidized to nitrates. As a result, mixtures of the corresponding cis-and trans-C-nitrates were obtained from the nnti-dimer of trans-l-nitroso-2-chlorocyclohexane. The anti-dimer of trans-I-nitroso-2-piperidinocyclohexane was photolytically tautomerized to the corresponding oxime under nitrogen and was oxidized chiefly to the C-nitro compound under oxygen; the two processes obviously share a common intermediate. Mechanisms for these photoprocesses are suggested.L'irradiation dans une atmosphere d'azote des dimeres-anti de composCs C-nitroso a provoquC la dissociation de ceux-ci pour donner le monomere C-nitroso correspondant lequel a subi une photodismutation, une tautomerisationet une dimkrisation. Une irradiation similairedans uneatmosphbre d'oxygeneaconduit principalement a la formation des produits nitrate et nitro. La dismutation de la N-(nitroso-4 hexyl) acCtamide se produit par photodissociation du monomere C-nitroso en radical alcoyle et en oxyde nitrique tel qu'il a CtC demontrt. Sous une atmosphere d'oxygene, ces composes C-nitroso qui peuvent subir une photodissociation facile ont CtC tres rapidement oxydCs en nitrates. Par suite, i partir du dimbre-crnti du trnns nitroso-l chloro-2 cyclohexane on a pu obtenir un mtlange des C-nitrates cis et anti correspondants. Le dimereonti du trans nitroso-1 piperidino-2cyclohexanea CtC tautomCrise photolytiquement pourdonner I'oxyme correspondant sous azote e t a CtC oxydC surtout en compose C-nitro sous oxygene; ces deux processus doivent necessairement possCder un intermkdiaire commun. Par suite, on suggere des mecanismes pour ces procCdes photochimiques.[Traduit par le journal]Can.

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Section: Photodecompositionmentioning

confidence: 99%

Section: Photodecompositionmentioning

confidence: 99%

Photoreactions of Nitroso Compounds in Solution. XXIV. Photooxidation and Photodecomposition of C-Nitroso Compounds

Chow¹,

Tam²,

Pillay³

1973

Can. J. Chem.

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“…Irradiation of a sample of 12a with 100 consecutive laser pulses resulted in complete photolysis; the typical spectral change is shown in Figure 3. The characteristic absorption at 320 nm56 is caused by the formation of the azodioxide57 16 , the dimer of the nitroso compound. The typical absorption of the nitroso‐monomer around 750 nm had a very low extinction coefficient and could not be observed.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photophysical Characterization of a New, Highly Hydrophilic Caging Group

2002

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Keywords: Caged compounds / Glutamate transporter / Natural products / Photochemistry o-Nitrobenzyl-protected bioactive compounds are useful tools in biophysics, allowing controlled photorelease of biologically active compounds with high temporal and spatial precision. Thus, it is possible to study biological processes, such as neurotransmitter-receptor interaction, and many other processes, in much more detail than before. In this respect, these caged compounds have become established as extremely useful tools. In some cases, however, their biological properties (the caged compound should not interact with the biological system), their photochemical properties (quantum yield and kinetics of the photorelease), and their physical properties (high hydrophilicity) are not satisfactory. In order

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“…Inspection of molecular models indicates that for 3 and 16 [and possibly 3 ( = 2) and 15 as well] the computed low-energy pathway is difficult to achieve. On the contrary, models suggest no unambiguous reason why the twisted transition state cannot be attained by 3 ( = 3, 4) and 10.…”

mentioning

confidence: 99%

Cis azoxy alkanes. VI. Cis azo N,N'-dioxide synthesis and the importance of entropy in the nitrosoalkane-azo dioxide equilibrium

Snyder¹,

Heyman²,

Suciu³

1975

J. Org. Chem.

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C-nitroso compounds. Part V. The preparation of cis-azodioxy compounds (cis-dimeric nitroso compounds)

Cited by 17 publications

References 9 publications

Photoreactions of Nitroso Compounds in Solution. XXIV. Photooxidation and Photodecomposition of C-Nitroso Compounds

Photoreactions of Nitroso Compounds in Solution. XXIV. Photooxidation and Photodecomposition of C-Nitroso Compounds

Synthesis and Photophysical Characterization of a New, Highly Hydrophilic Caging Group

Cis azoxy alkanes. VI. Cis azo N,N'-dioxide synthesis and the importance of entropy in the nitrosoalkane-azo dioxide equilibrium

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