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 HerpelArch. Pharm. Pharm. Med. Chem. 331(3), 111-117 (1998)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.no-donor.pdf)
AbstractTwelve 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 IC
50 below 10 uM,
2a being the most active substance with an IC
50 = 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 N
2O, 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 YamadaChemistry Letters 505-506 (1995)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/alkene.nitration.no-1.pdf)
AbstractNitroolefins 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 MukaiyamaBull. Chem. Soc. Jpn., 68, 3629-3636(1995)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/alkene.nitration.no-2.pdf)
AbstractOlefins 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. PaiJ. Org. Chem. 18, 1253-1262 (1953)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.25-meo.pdf)
2,5-Dimethoxy-propenylbenzene pseudonitrosite____ ___ __ _
Über Pseudonitrosite, Nitroxime und Furoxane (05-03-04):Dieter Klamann, Wolfgang Koser, Peter Weyerstahl und Manfred FliggeChem. 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 AngeliChem. 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 AngeliChem. 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. WielandAnn. 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. WallachAnn. 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. WielandChem. 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 BrucknerJ. 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. VinklerJ. 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 BrucknerJ. 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 BrucknerAnn. 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. KrámliJ. 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. BrucknerJ. 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. KrámliArch. 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. KrámliJ. 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 FodorChem. Ber. 76, 466-479 (1943)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudonitrosite.bruckner.1943-ber466.pdf)