Pseudonitrosite Publications (1891-1998)

[Rhodium]

Here I will collect the all articles ever published on the topic of Pseudonitrosite adducts of propenylbenzenes, and any other article of significance to that topic (even if it mainly deals with pseudonitrosite derivatives of other alkenes). Please PM me if you know of any omissions (I estimate the current collection to comprise well over half of the above scope). I will add summaries of the most important findings in each of the articles (including a list of prepared compounds of interest) when I have the time. If you want to help out with this, send your summaries to me.


Recent Pseudonitrosite Articles (in English)

_{New NO-Donors with Antithrombotic and Vasodilating Activities, Part 21}
Pseudonitrosites and Other Azodioxides with Vicinal Electron Acceptors (04-29-04):
Klaus Rehse and Martin Herpel

Arch. Pharm. Pharm. Med. Chem. 331(3), 111-117 (1998)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.no-donor.pdf)

Abstract
Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a–h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test, collagen). Four of them showed an IC₅₀ below 10 uM, 2a being the most active substance with an IC₅₀ = 2.1 uM. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound (18% inhibition in arterioles). The in vitro decomposition of 2a at 37°C gave NO and N₂O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron acceptors i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b,c).
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Convenient and Simple Preparation of Nitroolefins Nitration of Olefins with Nitric Oxide (04-19-04):
Teruaki Mukaiyama, Eiichiro Hata, and Tohru Yamada

Chemistry Letters 505-506 (1995)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/alkene.nitration.no-1.pdf)

Abstract
Nitroolefins are conveniently prepared in high yields by nitration of olefins under an atmospheric pressure of nitric oxide at room temperature and subsequent treatment with acidic alumina.
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A Convenient Method for the Preparation of Nitro Olefins by Nitration of Olefins with Nitrogen Monoxide (04-19-04):
Eiichiro Hata, Tohru Yamada, and Teruaki Mukaiyama

Bull. Chem. Soc. Jpn., 68, 3629-3636(1995)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/alkene.nitration.no-2.pdf)

Abstract
Olefins with a terminal double bond or conjugated with aromatic nucleus are successfully nitrated into nitro olefins in good-to-high yields on treatment with nitrogen monoxide (NO) in 1,2-dichloroethane. Nitro alcohols formed as by-products are dehydrated to yield nitro olefins by the subsequent treatment with acidic activated alumina. By GC analysis, it was confirmed that an equimolar amount of nitrogen gas was evolved during the present nitration. A possible reaction pathway including the formation of nitro nitroso compounds, key intermediates, is described. The key intermediates are transformed into nitro olefins by reaction with nitrogen monoxide.


Other Pseudonitrosite Articles (in English or German)

Synthesis of 3-Methyl Isoquinolines (04-29-04):
T. R. Govindachari, B. R. Pai

J. Org. Chem. 18, 1253-1262 (1953)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.25-meo.pdf)

2,5-Dimethoxy-propenylbenzene pseudonitrosite
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Über Pseudonitrosite, Nitroxime und Furoxane (05-03-04):
Dieter Klamann, Wolfgang Koser, Peter Weyerstahl und Manfred Fligge

Chem. Ber. 98, 1831-1836 (1965)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.klamann.1965-ber1831.pdf)


Vintage Pseudonitrosite Articles (in German)

Ueber die Einwirkung der salpetrigen Säure auf einige ungesättigte Verbindungen der aromatischen Reihe. I. Mitteilung. (04-29-04):
Angelo Angeli

Chem. Ber. 24, 3994-3996 (1891)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.angeli-1891.pdf)
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Ueber die Einwirkung der salpetrigen Säure auf einige ungesättigte Verbindungen der aromatischen Reihe. I. Mitteilung. (04-29-04):
Angelo Angeli

Chem. Ber. 25, 1956-1963 (1892)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.angeli-1892.pdf)
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Zur Kenntniss der Pseudonitrosite (05-13-04):
H. Wieland

Ann. Chem. 329, 225-268 (1903)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.wieland.1903-ann225.pdf)
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Ueber die Additionsproducte von N₂O₃ und von NOCl (05-03-04):
O. Wallach

Ann. Chem. 332, 305-336 (1904)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.wallach.1903-ann305.pdf)
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Zur Kenntnis der sogenannte Styrolnitrosite. Ueber eine neue Bildungsweise der untersalpetrigen Säure (05-03-04):
H. Wieland

Chem. Ber. 36, 2558-2567 (1903)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.wieland.1903-ber2558.pdf)
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Über das Pseudonitrosit des Asarons (04-29-04):
Viktor Bruckner

J. Prakt. Chem. 138, 268-274 (1933)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1933-jpc268.pdf)
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_{Über eine neue Umwandlung der Pseudonitrosite propenylhaltiger Phenoläther}
Eine neue Synthese von ?-(Alkoxy-phenyl)-?-nitro-propanolen bzw. deren Methyläther (04-29-04):
V. Bruckner und E. Vinkler

J. Prakt. Chem. 142, 277-290 (1935)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1935-jpc277.pdf)
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Über die Alkaliempfindlichkeit von ?-(Alkoxy-phenyl)-?-amino- und -hydroxylamino-propanolen (04-29-04):
Viktor Bruckner

J. Prakt. Chem. 142, 301-309 (1935)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1935-jpc301.pdf)
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_{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on ?-arylierten ?-Hydroxylamino- und ?-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.}
I. Mitteilung. Methyl-isoeugenol- und Isosafrol-Derivate (04-29-04):
Viktor Bruckner

Ann. Chem. 518, 226-244 (1935)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1935-ann226.pdf)
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_{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on ?-arylierten ?-Hydroxylamino- und ?-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.}
II. Mitteilung. Isoeugenolderivate. (04-29-04):
V. Bruckner und A. Krámli

J. Prakt. Chem. 143, 287-297 (1935)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1935-jpc287.pdf)
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_{Über die Verwendung der Pseudo-nitrosite propenyl-haltiger Phenol-äther zur Synthese on ?-arylierten ?-Hydroxylamino- und ?-Amino-propanolen. Neue Beiträge zur Kenntnis der Acylwanderungen.}
III. Mitteilung. Anetholderivate (04-29-04):
A. Krámli und V. Bruckner

J. Prakt. Chem. 148, 117-125 (1937)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1937-jpc117.pdf)
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Über eine neue Synthese von Ephedrinabkömmlingen (04-29-04):
V. Bruckner und A. Krámli

Arch. Pharm. 273, 372-384 (1935)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1935-ap372.pdf)
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Über eine neue Synthese von Abkömmlingen des 3-Methyl-Isochinolins (04-29-04):
V. Bruckner und A. Krámli

J. Prakt. Chem. 145, 291-300 (1936)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1936-jpc291.pdf)
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Über eine neue Synthese des ?-[3,4-Dioxy-phenyl]-?-amino-propanols (05-13-04):
V. Bruckner und G. von Fodor

Chem. Ber. 76, 466-479 (1943)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1943-ber466.pdf)