DOI: 10.1002/ange.19650771104. Neuere Methoden der präparativen organischen Chemie IV. Isonitril-Synthesen

Neuere Methoden der präparativen organischen Chemie IV. Isonitril-Synthesen

10.1002/ange.19650771104

Crossref journal-article

Wiley

Angewandte Chemie (311)

Bibliography

Ugi, I., Fetzer, U., Eholzer, U., Knupfer, H., & Offermann, K. (1965). Neuere Methoden der prÃ¤parativen organischen Chemie IV. Isonitril-Synthesen. Angewandte Chemie, 77(11), 492â504.

Authors 5

I. Ugi (first)
U. Fetzer (additional)
U. Eholzer (additional)
H. Knupfer (additional)
K. Offermann (additional)

References 195 Referenced 205

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Die Ausbeuten der Carbylamin-Reaktion betragen bei Verwendung von äthanolischer Kalilauge als Base maximal 20%, mit festem Alkali bis zu 45%, und mit Kalium-tert.-butylat wer den bis zu 55% erreicht. In der Literatur (u. a. [32, 35, 36a]) angegebene wesentlich höhere Ausbeuten dürften sich auf Gemische von Isonitrilen und primären Aminen beziehen.
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Beispielsweise sind 2.4-Dinitro-phenylisonitril und 1.4-Dichlor-2.5-diisocyanbenzol nicht zugänglich.
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Wir danken Frau Dr. D. Lauerer und Herrn Prof. Dr. M. Pestemer für IR-Messungen. Die Herren Dr. E. Degener, Dr. H. Eck, Dr. H. Herlinger, Dr. H. Holtschmidt, Dr. F. Möller, Dr. J. A. Renner, Dr. K. W. Schellhammer, Dr. R. Schröter, Dr. H. Tarnow, Dr. H. Wilms und Dr. W. Zecher stellten freundlicherweise Ausgangsmaterialien zur Verfügung. Den Herren , , , , und schulden wir Dank für ihre Hilfe bei der Durchführung der Versuche. by Holstein
Die Anordnung der Substanzen erfolgte nach der Anzahl der enthaltenen C-, H-, Br-, Cl-, F-, N-, O-, P- und S-Atome. „n.d.” steht für „nicht destillierbares Öl”, „Z. ”bedeutet „unter Zersetzung”.
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Die verwendeten tert.-Amine müssen frei von Wasser und acylierbaren Aminen sein. Der Chlorwasserstoffgehalt des Phosgens sollte gering sein. N-Alkyl-formamide sind in der Regel aus prim. aliphatischen Aminen und der berechneten Menge technischer 70-bis 95-proz. Ameisensäure durch Erhitzen in Chlorbenzol, Toluol oder Xylol und Abdestillieren des Reaktionswassers mit einem Veresterungsaufsatz bequem zugänglich. N-Arylformamide erhält man aus prim. Arylaminen durch 2–15 stdg. Erhitzen (70–105°C) mit der 2- bis 10-fachen Gewichtsmenge 85- bis 100-proz. Ameisensäure. Die als Ausgangsmaterialien dienenden Formamide dürfen weder Ameisensäure noch Dimethylformamid enthalten; schwerlösliche Formamide werden vor der Umsetzung mit Hilfe eines „Ultra-Turrax” [55] in Suspension gründlich zerkleinert. Für die Trocknung von Isonitrillösungen eignen sich u. a. wasserfreies Kaliumcarbonat oder Magneisiumsulfat. Beim Einengen von Isonitrillösungen sollten Badtemperaturen >50°C vermieden werden. b) Von wenigen Ausnahmen abgesehen, weisen Isonitrile für Warmblütler keine nennenswerte Toxizität auf (vgl. [1a]). Wie im toxikologischen Laboratorium der Farbenfabriken Bayer AG., Elberfeld, festgestellt wurde, werden Dosen von 500–5000 mg/kg (Maus, oral und subkutan) vertragen. Über die ausgeprägten fungiciden, acariciden und insekticiden Eigenschaften von Isonitrilen finden sich Angaben im Belg. Pat. 641379 (12. 6. 1964/Dt. Prior. 17. 12. 1962), Farbenfabriken Bayer AG.; Erf.: , , , , , u. ;
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in : Molecular Rearrangements. Interscience Publishers, New York 1963, S. 457. / Molecular Rearrangements by Smith (1963)
10.1021/jo01351a010 / J. org. Chemistry by Mukaijama (1961)
10.1246/bcsj.33.1382 / Bull. chem. Soc. (Japan) by Mukaijama (1960)
10.1002/cber.19620950122 / Chem. Ber. by Ugi (1962)
10.1002/cber.19050380109 / Ber. dtsch. chem. Ges. by Werner (1905)
10.1248/cpb.9.635 / Chem. pharmac. Bull. (Tokyo) by Higashino (1961)
10.1002/cber.191504801129 / Ber. dtsch. chem. Ges. by Madelung (1915)
„Dimeres Phenylisocyanid”, das sich möglicherweise in sehr geringer Konzentration mit Phenylisocyanid im Gleichgewicht befindet, ist wohl auch als Zwischenstufe der 2-Hydroxyl-1-naphthylglyoxal-Synthese [102] anzusehen.
{'key': '10.1002/ange.19650771104-BIB129.1', 'first-page': '185', 'volume': '54', 'author': 'Passerini', 'year': '1924', 'journal-title': 'Gazz. chim. ital.'} / Gazz. chim. ital. by Passerini (1924)
{'key': '10.1002/ange.19650771104-BIB129.2', 'first-page': '555', 'volume': '55', 'year': '1925', 'journal-title': 'Gazz. chim. ital.'} / Gazz. chim. ital. (1925)
{'key': '10.1002/ange.19650771104-BIB129.3', 'first-page': '934', 'volume': '64', 'author': 'Passerini', 'year': '1934', 'journal-title': 'Gazz. chim. ital.'} / Gazz. chim. ital. by Passerini (1934)
10.1002/cber.19580910705 / Chem. Ber. by Grundmann (1958)
{'key': '10.1002/ange.19650771104-BIB131', 'first-page': '3192', 'volume': '255', 'author': 'Abraham', 'year': '1962', 'journal-title': 'C. R. hebd. Séances Acad. Sci.'} / C. R. hebd. Séances Acad. Sci. by Abraham (1962)
10.1021/ja01068a041 / J. Amer. chem. Soc. by Newman (1964)
10.1021/ja01058a052 / J. Amer. chem. Soc. by Sheehan (1964)
10.1021/ja01061a018 / J. Amer. chem. Soc. by Sheehan (1964)
unveröffentlichte Versuche. by Ugi
{'key': '10.1002/ange.19650771104-BIB136', 'first-page': '3058', 'volume': '1960', 'author': 'Farrar', 'journal-title': 'J. chem. Soc. (London)'} / J. chem. Soc. (London) by Farrar
10.1016/0040-4020(58)88025-4 / Tetrahedron by Doering (1958)
10.1021/jo01081a054 / J. org. Chemistry by Moore (1960)
{'key': '10.1002/ange.19650771104-BIB137.3', 'first-page': '4129', 'volume': '27', 'year': '1962', 'journal-title': 'J. org. Chemistry'} / J. org. Chemistry (1962)
{'key': '10.1002/ange.19650771104-BIB137.4', 'first-page': '167', 'volume': '1961', 'author': 'Skatteböl', 'journal-title': 'Tetrahedron Letters'} / Tetrahedron Letters by Skatteböl
{'key': '10.1002/ange.19650771104-BIB137.5', 'first-page': '173', 'volume': '1961', 'author': 'Logan', 'journal-title': 'Tetrahedron Letters'} / Tetrahedron Letters by Logan
{'key': '10.1002/ange.19650771104-BIB137.6', 'first-page': '143', 'volume': '1961', 'author': 'Ball', 'journal-title': 'Proc. chem. Soc. (London)'} / Proc. chem. Soc. (London) by Ball
{'key': '10.1002/ange.19650771104-BIB137.7', 'first-page': '2298', 'volume': '1962', 'journal-title': 'J. chem. Soc. (London)'} / J. chem. Soc. (London)
10.1021/jo01067a609 / J. org. Chemistry by Gardner (1961)
10.1021/jo01059a014 / J. org. Chemistry by Moore (1962)

Dates

Type	When
Created	18 years, 1 month ago (July 14, 2007, 5:13 p.m.)
Deposited	1 year, 6 months ago (Feb. 16, 2024, 11:52 a.m.)
Indexed	2 weeks, 3 days ago (Aug. 7, 2025, 4:45 p.m.)
Issued	60 years, 2 months ago (June 7, 1965)
Published	60 years, 2 months ago (June 7, 1965)
Published Print	60 years, 2 months ago (June 7, 1965)

Funders 0

None

BibTeX

@article{Ugi_1965, title={Neuere Methoden der präparativen organischen Chemie IV. Isonitril-Synthesen}, volume={77}, ISSN={1521-3757}, url={http://dx.doi.org/10.1002/ange.19650771104}, DOI={10.1002/ange.19650771104}, number={11}, journal={Angewandte Chemie}, publisher={Wiley}, author={Ugi, I. and Fetzer, U. and Eholzer, U. and Knupfer, H. and Offermann, K.}, year={1965}, month=jun, pages={492–504} }

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      "key": "10.1002/ange.19650771104-BIB33",
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      "volume": "1",
      "author": "Malatesta",
      "year": "1959",
      "journal-title": "Progr. inorg. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB34",
      "doi-asserted-by": "crossref",
      "first-page": "3226",
      "DOI": "10.1021/jo01067a672",
      "volume": "26",
      "author": "Heldt",
      "year": "1961",
      "journal-title": "J. org. Chemistry"
    },
    {
      "key": "10.1002/ange.19650771104-BIB35.1",
      "first-page": "237",
      "volume": "53/54",
      "author": "H\u00f6lzl",
      "year": "1929",
      "journal-title": "Mh. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB35.2",
      "first-page": "97",
      "volume": "64",
      "author": "H\u00f6lzl",
      "year": "1934",
      "journal-title": "Mh. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB36",
      "first-page": "319",
      "volume": "43",
      "author": "H\u00f6lzl",
      "year": "1937",
      "journal-title": "Z. Elektrochem. angew. physik. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB37",
      "unstructured": "Bromoform [26] und Jodoform [27] sind weniger geeignet."
    },
    {
      "key": "10.1002/ange.19650771104-BIB38",
      "doi-asserted-by": "crossref",
      "first-page": "1998",
      "DOI": "10.1021/ja01289a059",
      "volume": "59",
      "author": "Davis",
      "year": "1937",
      "journal-title": "J. Amer. chem. Soc."
    },
    {
      "key": "10.1002/ange.19650771104-BIB39",
      "first-page": "376",
      "volume": "35",
      "author": "Bose",
      "year": "1958",
      "journal-title": "Chem. Soc."
    },
    {
      "key": "10.1002/ange.19650771104-BIB40",
      "first-page": "340",
      "volume": "50 II",
      "author": "Passerini",
      "year": "1920",
      "journal-title": "Gazz. chim. ital."
    },
    {
      "key": "10.1002/ange.19650771104-BIB41",
      "first-page": "636",
      "volume": "58",
      "author": "Passerini",
      "year": "1928",
      "journal-title": "Gazz. chim. ital."
    },
    {
      "key": "10.1002/ange.19650771104-BIB42",
      "doi-asserted-by": "crossref",
      "first-page": "351",
      "DOI": "10.1021/ja01463a022",
      "volume": "83",
      "author": "Cotton",
      "year": "1961",
      "journal-title": "J. Amer. chem. Soc."
    },
    {
      "key": "10.1002/ange.19650771104-BIB43",
      "doi-asserted-by": "crossref",
      "first-page": "1",
      "DOI": "10.1002/jlac.19003100102",
      "volume": "310",
      "author": "Biddle",
      "year": "1900",
      "journal-title": "Liebigs Ann. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB44",
      "first-page": "238",
      "volume": "77",
      "author": "Malatesta",
      "year": "1947",
      "journal-title": "Gazz. chim. ital."
    },
    {
      "key": "10.1002/ange.19650771104-BIB45",
      "doi-asserted-by": "crossref",
      "first-page": "1599",
      "DOI": "10.1021/jo01105a002",
      "volume": "23",
      "author": "Smith",
      "year": "1958",
      "journal-title": "J. org. Chemistry"
    },
    {
      "key": "10.1002/ange.19650771104-BIB46.1",
      "author": "Ross",
      "year": "1957",
      "unstructured": "Dissertation, Universit\u00e4t M\u00fcnchen, 1957;"
    },
    {
      "key": "10.1002/ange.19650771104-BIB46.2",
      "author": "Dellmayer",
      "year": "1959",
      "unstructured": "Diplomarbeit, Universit\u00e4t M\u00fcnchen, 1959."
    },
    {
      "key": "10.1002/ange.19650771104-BIB47",
      "doi-asserted-by": "crossref",
      "first-page": "617",
      "DOI": "10.1246/bcsj.36.617",
      "volume": "36",
      "author": "Shingaki",
      "year": "1963",
      "journal-title": "Bull. chem. Soc. (Japan)"
    },
    {
      "key": "10.1002/ange.19650771104-BIB48",
      "unstructured": "Die Ausbeuten der Carbylamin-Reaktion betragen bei Verwendung von \u00e4thanolischer Kalilauge als Base maximal 20%, mit festem Alkali bis zu 45%, und mit Kalium-tert.-butylat wer den bis zu 55% erreicht. In der Literatur (u. a. [32, 35, 36a]) angegebene wesentlich h\u00f6here Ausbeuten d\u00fcrften sich auf Gemische von Isonitrilen und prim\u00e4ren Aminen beziehen."
    },
    {
      "key": "10.1002/ange.19650771104-BIB49",
      "doi-asserted-by": "crossref",
      "first-page": "1323",
      "DOI": "10.1002/cber.188802101250",
      "volume": "21",
      "author": "Schneidewind",
      "year": "1888",
      "journal-title": "Ber. dtsch. chem. Ges."
    },
    {
      "key": "10.1002/ange.19650771104-BIB50",
      "doi-asserted-by": "crossref",
      "first-page": "184",
      "DOI": "10.1002/jlac.19244360111",
      "volume": "436",
      "author": "Rupe",
      "year": "1924",
      "journal-title": "Liebigs Ann. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB51.",
      "unstructured": "US.-Pat. 2342794 (29. Febr. 1944) u."
    },
    {
      "key": "crKey-10.1002/ange.19650771104-BIB72",
      "unstructured": "US.-Pat. 2347772 (2. Mai 1944), beide Celanese Corp., Erf.:"
    },
    {
      "key": "10.1002/ange.19650771104-BIB52",
      "doi-asserted-by": "crossref",
      "first-page": "376",
      "DOI": "10.1021/jo01109a613",
      "volume": "21",
      "author": "Samuel",
      "year": "1956",
      "journal-title": "J. org. Chemistry"
    },
    {
      "key": "10.1002/ange.19650771104-BIB53",
      "doi-asserted-by": "crossref",
      "first-page": "1107",
      "DOI": "10.1021/jo01102a005",
      "volume": "23",
      "author": "Feuer",
      "year": "1958",
      "journal-title": "J. org. Chemistry"
    },
    {
      "key": "10.1002/ange.19650771104-BIB54",
      "doi-asserted-by": "crossref",
      "first-page": "388",
      "DOI": "10.1007/BF02639612",
      "volume": "36",
      "author": "Jungermann",
      "year": "1959",
      "journal-title": "J. Amer. Oil Chemists' Soc."
    },
    {
      "key": "10.1002/ange.19650771104-BIB55",
      "first-page": "419",
      "volume-title": "Lehrbuch der Oranischen Chemie",
      "volume": "I/1",
      "author": "Meyer",
      "year": "1922",
      "unstructured": "Vgl. auch: u. , Lehrbuch der Oranischen Chemie. der Gruyter, Leipzig 1922, Bd. I/1, S. 419."
    },
    {
      "key": "10.1002/ange.19650771104-BIB56.1",
      "doi-asserted-by": "crossref",
      "first-page": "2438",
      "DOI": "10.1021/ja01162a024",
      "volume": "72",
      "author": "Hine",
      "year": "1950",
      "journal-title": "J. Amer. chem. Soc."
    },
    {
      "key": "10.1002/ange.19650771104-BIB56.2",
      "doi-asserted-by": "crossref",
      "first-page": "6162",
      "DOI": "10.1021/ja01652a087",
      "volume": "76",
      "author": "Doering",
      "year": "1954",
      "journal-title": "J. Amer. chem. Soc."
    },
    {
      "key": "10.1002/ange.19650771104-BIB57",
      "unstructured": "Auch sekund\u00e4re und terti\u00e4re Amine lagern in analoger Weise Dichlorcarben an, jedoch unterbleibt die Eliminierung von Chlorwasserstoff [40,41]."
    },
    {
      "key": "10.1002/ange.19650771104-BIB58.1",
      "doi-asserted-by": "crossref",
      "first-page": "88",
      "DOI": "10.1016/0040-4020(59)80038-7",
      "volume": "6",
      "author": "Saunders",
      "year": "1959",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "10.1002/ange.19650771104-BIB58.2",
      "doi-asserted-by": "crossref",
      "first-page": "1",
      "DOI": "10.1016/0040-4020(60)89001-1",
      "volume": "11",
      "year": "1960",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "10.1002/ange.19650771104-BIB58.3",
      "doi-asserted-by": "crossref",
      "first-page": "5",
      "DOI": "10.1016/S0040-4039(01)82724-6",
      "volume": "7",
      "author": "Frankel",
      "year": "1959",
      "journal-title": "Tetrahedron Letters"
    },
    {
      "key": "10.1002/ange.19650771104-BIB59",
      "first-page": "901",
      "volume": "14",
      "author": "Ploquin",
      "year": "1947",
      "journal-title": "Bull. Soc. chim. France (5)"
    },
    {
      "key": "10.1002/ange.19650771104-BIB60",
      "doi-asserted-by": "crossref",
      "first-page": "1089",
      "DOI": "10.1021/jo01050a541",
      "volume": "27",
      "author": "Krapcho",
      "year": "1962",
      "journal-title": "J. org. Chemistry"
    },
    {
      "key": "10.1002/ange.19650771104-BIB61",
      "first-page": "203",
      "volume": "1960",
      "author": "Beichl",
      "journal-title": "Chem. and Ind."
    },
    {
      "key": "10.1002/ange.19650771104-BIB62",
      "author": "Wegler",
      "unstructured": "pers\u00f6nliche Mitteilung."
    },
    {
      "key": "10.1002/ange.19650771104-BIB63",
      "first-page": "409",
      "volume": "11",
      "author": "Hagedorn",
      "year": "1956",
      "journal-title": "Pharmazie"
    },
    {
      "key": "10.1002/ange.19650771104-BIB64",
      "first-page": "567",
      "volume": "12",
      "author": "Hagedorn",
      "year": "1957",
      "journal-title": "Pharmazie"
    },
    {
      "key": "10.1002/ange.19650771104-BIB65",
      "doi-asserted-by": "crossref",
      "first-page": "1584",
      "DOI": "10.1002/cber.19600930720",
      "volume": "93",
      "author": "Hagedorn",
      "year": "1960",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "10.1002/ange.19650771104-BIB66",
      "first-page": "190",
      "volume": "5",
      "author": "Rothe",
      "year": "1950",
      "journal-title": "Pharmazie"
    },
    {
      "key": "10.1002/ange.19650771104-BIB67",
      "doi-asserted-by": "crossref",
      "first-page": "239",
      "DOI": "10.1002/cber.19600930136",
      "volume": "93",
      "author": "Ugi",
      "year": "1960",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "10.1002/ange.19650771104-BIB68",
      "doi-asserted-by": "crossref",
      "first-page": "702",
      "DOI": "10.1002/ange.19580702213",
      "volume": "70",
      "author": "Ugi",
      "year": "1958",
      "journal-title": "Angew. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB69",
      "unstructured": "DAS 1158499 (2. M\u00e4rz 1962/5. Dez. 1963), Farbenfabriken Bayer AG., Erf.: u. ."
    },
    {
      "key": "10.1002/ange.19650771104-BIB70.1",
      "doi-asserted-by": "crossref",
      "first-page": "2814",
      "DOI": "10.1002/cber.19610941033",
      "volume": "94",
      "author": "Ugi",
      "year": "1961",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "10.1002/ange.19650771104-BIB70.",
      "unstructured": "DAS 1177146 (3. Aug. 1960/ 3. Sept. 1964), Erf.: u. ."
    },
    {
      "key": "10.1002/ange.19650771104-BIB71",
      "author": "Knupfer",
      "unstructured": "Dtsch. Pat.-Anm., Farbenfabriken Bayer AG., Erf.: , u. ."
    },
    {
      "key": "10.1002/ange.19650771104-BIB72",
      "unstructured": "Dtsch. Pat.-Anm., Farbenfabriken Bayer AG., Erf.: I. Ugi."
    },
    {
      "key": "10.1002/ange.19650771104-BIB73",
      "unstructured": "Auch gro\u00dfe Ans\u00e4tze (10\u2013100 Mol) erfordern einschlie\u00dflich der Aufarbeitung nicht mehr als 8\u201315 Std. Arbeitszeit; Ausbeuten bis zu 97%; wohlfeile Hilfsstoffe."
    },
    {
      "key": "10.1002/ange.19650771104-BIB74",
      "unstructured": "DAS 1158500 (6. April 1962/ 5. Dez. 1963), Farbenfabriken Bayer AG., Erf.:"
    },
    {
      "key": "10.1002/ange.19650771104-BIB75",
      "unstructured": "Das abdestillierte Tri\u00e4thylamin/Methylenchlorid kann ohne Reinigung f\u00fcr analoge Ans\u00e4tze weiterverwendet werden."
    },
    {
      "key": "10.1002/ange.19650771104-BIB76",
      "unstructured": "Janke & Kunkel KG., Staufen i. Br."
    },
    {
      "key": "10.1002/ange.19650771104-BIB77",
      "unstructured": "Auch die nach der Hofmann-Methode (s. Abschn. 3) nicht zug\u00e4nglichen [33] N-Isocyan-dialkylamine sind mit der Phosgen-Methode dargestellt worden [57]."
    },
    {
      "key": "10.1002/ange.19650771104-BIB78.1",
      "doi-asserted-by": "crossref",
      "first-page": "388",
      "DOI": "10.1002/ange.19620741109",
      "volume": "74",
      "author": "Bredereck",
      "year": "1962",
      "journal-title": "Angew. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB78.2",
      "first-page": "580",
      "volume": "76",
      "year": "1964",
      "journal-title": "Angew. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB78.3",
      "first-page": "334",
      "volume": "1",
      "year": "1962",
      "journal-title": "Angew. Chem. internat. Edit."
    },
    {
      "key": "10.1002/ange.19650771104-BIB78.4",
      "first-page": "647",
      "volume": "3",
      "year": "1964",
      "journal-title": "Angew. Chem. internat. Edit."
    },
    {
      "key": "10.1002/ange.19650771104-BIB79",
      "unstructured": "Beispielsweise sind 2.4-Dinitro-phenylisonitril und 1.4-Dichlor-2.5-diisocyanbenzol nicht zug\u00e4nglich."
    },
    {
      "key": "10.1002/ange.19650771104-BIB80",
      "unstructured": "p-Amino-, p-Carboxy- und p-Sulfonamido-phenylisonitril, die durch die Carbylamin-Reaktion zug\u00e4nglich sind [9,36d], lassen sich nach der Phosgen-Methode nicht darstellen. Allgemein sind Isonitrile in Abwesenheit von Basen [60] gegen\u00fcber Phosgen sehr reaktionsf\u00e4hig [5b, 61]."
    },
    {
      "key": "10.1002/ange.19650771104-BIB81",
      "first-page": "3146",
      "volume": "1963",
      "author": "Sayigh",
      "journal-title": "J. chem. Soc. (London)"
    },
    {
      "key": "10.1002/ange.19650771104-BIB82",
      "doi-asserted-by": "crossref",
      "first-page": "1116",
      "DOI": "10.1002/cber.19610940433",
      "volume": "94",
      "author": "Ugi",
      "year": "1961",
      "journal-title": "Chem. Ber."
    },
    {
      "key": "10.1002/ange.19650771104-BIB83",
      "author": "Holstein",
      "unstructured": "Wir danken Frau Dr. D. Lauerer und Herrn Prof. Dr. M. Pestemer f\u00fcr IR-Messungen. Die Herren Dr. E. Degener, Dr. H. Eck, Dr. H. Herlinger, Dr. H. Holtschmidt, Dr. F. M\u00f6ller, Dr. J. A. Renner, Dr. K. W. Schellhammer, Dr. R. Schr\u00f6ter, Dr. H. Tarnow, Dr. H. Wilms und Dr. W. Zecher stellten freundlicherweise Ausgangsmaterialien zur Verf\u00fcgung. Den Herren , , , , und schulden wir Dank f\u00fcr ihre Hilfe bei der Durchf\u00fchrung der Versuche."
    },
    {
      "key": "10.1002/ange.19650771104-BIB84",
      "unstructured": "Die Anordnung der Substanzen erfolgte nach der Anzahl der enthaltenen C-, H-, Br-, Cl-, F-, N-, O-, P- und S-Atome. \u201en.d.\u201d steht f\u00fcr \u201enicht destillierbares \u00d6l\u201d, \u201eZ. \u201dbedeutet \u201eunter Zersetzung\u201d."
    },
    {
      "key": "10.1002/ange.19650771104-BIB85",
      "unstructured": "Die durch \u201ea\u201d\u2013\u201ep\u201d gekennzeichneten Ausbeuten wurden unter Reaktionsbedingungen erhalten, die den Arbeitsvorschriften 4.112, a\u2013p entsprechen."
    },
    {
      "key": "10.1002/ange.19650771104-BIB86.1",
      "doi-asserted-by": "crossref",
      "first-page": "440",
      "DOI": "10.1002/ange.19640761023",
      "volume": "76",
      "author": "Neidlein",
      "year": "1964",
      "journal-title": "Angew. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB86.2",
      "first-page": "382",
      "volume": "3",
      "year": "1964",
      "journal-title": "Angew. Chem. internat. Edit."
    },
    {
      "key": "10.1002/ange.19650771104-BIB87.1",
      "doi-asserted-by": "crossref",
      "first-page": "500",
      "DOI": "10.1002/ange.19640761118",
      "volume": "76",
      "author": "Neidlein",
      "year": "1964",
      "journal-title": "Angew. Chem."
    },
    {
      "key": "10.1002/ange.19650771104-BIB87.2",
      "first-page": "446",
      "volume": "3",
      "year": "1964",
      "journal-title": "Angew. Chem. internat. Edit."
    },
    {
      "key": "10.1002/ange.19650771104-BIB88",
      "doi-asserted-by": "crossref",
      "first-page": "589",
      "DOI": "10.1002/ardp.19642971003",
      "volume": "297",
      "author": "Neidlein",
      "year": "1964",
      "journal-title": "Arch. Pharm."
    },
    {
      "key": "10.1002/ange.19650771104-BIB89",
      "author": "Herlinger",
      "unstructured": "F\u00fcr (S)-\u03b1-Phenyl\u00e4thyl-isonitril (aus (S)-(-)-\u03b1-Phenyl\u00e4thylamin) betr\u00e4gt laut pers\u00f6nlicher Mitteilung von [\u03b1]D22 = \u221249,5\u00b0 (vgl. [36b])."
    },
    {
      "key": "10.1002/ange.19650771104-BIB90.",
      "unstructured": "Die verwendeten tert.-Amine m\u00fcssen frei von Wasser und acylierbaren Aminen sein. Der Chlorwasserstoffgehalt des Phosgens sollte gering sein. N-Alkyl-formamide sind in der Regel aus prim. aliphatischen Aminen und der berechneten Menge technischer 70-bis 95-proz. Ameisens\u00e4ure durch Erhitzen in Chlorbenzol, Toluol oder Xylol und Abdestillieren des Reaktionswassers mit einem Veresterungsaufsatz bequem zug\u00e4nglich. N-Arylformamide erh\u00e4lt man aus prim. Arylaminen durch 2\u201315 stdg. Erhitzen (70\u2013105\u00b0C) mit der 2- bis 10-fachen Gewichtsmenge 85- bis 100-proz. Ameisens\u00e4ure. Die als Ausgangsmaterialien dienenden Formamide d\u00fcrfen weder Ameisens\u00e4ure noch Dimethylformamid enthalten; schwerl\u00f6sliche Formamide werden vor der Umsetzung mit Hilfe eines \u201eUltra-Turrax\u201d [55] in Suspension gr\u00fcndlich zerkleinert. F\u00fcr die Trocknung von Isonitrill\u00f6sungen eignen sich u. a. wasserfreies Kaliumcarbonat oder Magneisiumsulfat. Beim Einengen von Isonitrill\u00f6sungen sollten Badtemperaturen >50\u00b0C vermieden werden. b) Von wenigen Ausnahmen abgesehen, weisen Isonitrile f\u00fcr Warmbl\u00fctler keine nennenswerte Toxizit\u00e4t auf (vgl. [1a]). Wie im toxikologischen Laboratorium der Farbenfabriken Bayer AG., Elberfeld, festgestellt wurde, werden Dosen von 500\u20135000 mg/kg (Maus, oral und subkutan) vertragen. \u00dcber die ausgepr\u00e4gten fungiciden, acariciden und insekticiden Eigenschaften von Isonitrilen finden sich Angaben im Belg. Pat. 641379 (12. 6. 1964/Dt. Prior. 17. 12. 1962), Farbenfabriken Bayer AG.; Erf.: , , , , , u. ;"
    },
    {
      "key": "crKey-10.1002/ange.19650771104-BIB121",
      "unstructured": "Span. Pat. 294587 sowie 294588 (7. 2. 1964, dt. Prior.: 17. 12. 1962) und"
    },
    {
      "key": "crKey-10.1002/ange.19650771104-BIB122",
      "unstructured": "Belg. Pat. 641309 sowie 641311 (12. 6. 1964/dt. Prior. 17. 12. 1962), Farbenfabriken Bayer AG., Erf.: , , , und ; vgl. auch [68, 74]."
    },
    {
      "key": "10.1002/ange.19650771104-BIB91",
      "unstructured": "US.-Pat. 3012932 (12. Dez. 1961), Standard Oil of Indiana, Erf.: F. Bussert."
    },
    {
      "key": "10.1002/ange.19650771104-BIB92",
      "doi-asserted-by": "crossref",
      "first-page": "219",
      "DOI": "10.1002/ange.19610730612",
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