Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
-
Abstract
The preparation of the vinylogue guanidinium salt 10c is described. The reaction of the vinylogue orthocarbonic acid amide derivative 12 with CH2-acidic compounds 14a–s affords the ketene aminals 15a–s. At room temperature the succinimide 19a is deprotonated by 12 to give the vinylogue salt 10e. The bis-ketene aminal 20 is formed in the reaction of 19a with 12 at elevated temperatures. Succinic acid esters 21 do not react cleanly with the orthoamide 12, but mixtures of ketene aminals 23 and bis-ketene aminals 22 are formed. From succinodinitrile (24) and 12 the bis-ketene aminal 25 could be obtained, which is also accessible by the action of the salt 10c with 24 in the presence of sodium hydride.
Dedicated to:
Professor Branko Stanovnik on the occasion of his 80th birthday.
Literatur
[1] Orthoamide und Iminiumsalze, XCII: W. Kantlehner, J. Mezger, R. Kreß. W. Frey, Z. Naturforsch. 2018, 73b, 437.10.1515/znb-2018-0011Search in Google Scholar
[2] H. Basset, Chem. News1863, 7, 158.Search in Google Scholar
[3] H. Basset, Liebigs Ann. Chem. 1864, 132, 54.10.1002/jlac.18641320106Search in Google Scholar
[4] H. Meerwein, W. Florian, N. Schön, G. Stopp, Liebigs Ann. Chem. 1961, 641, 1.10.1002/jlac.19616410102Search in Google Scholar
[5] H. Eilingsfeld, M. Seefelder, H. Weidinger, Angew. Chem.1960, 72, 836.10.1002/ange.19600722208Search in Google Scholar
[6] H. Eilingsfeld, M. Seefelder, H. Weidinger, Chem. Ber.1963, 96, 2899.10.1002/cber.19630961111Search in Google Scholar
[7] H. Bredereck, F. Effenberger, H. P. Bayerlein, Chem. Ber. 1964, 97, 1834.10.1002/cber.19640970709Search in Google Scholar
[8] W. Kantlehner, L. Kienitz, H. Jaus, H. Bredereck, Liebigs Ann. Chem.1979, 2089.10.1002/jlac.197919791219Search in Google Scholar
[9] W. Kantlehner, W. W. Mergen, Synthesis1979, 11, 343.10.1055/s-1979-28672Search in Google Scholar
[10] H. Weingarten, W. A. White, J. Am. Chem. Soc. 1966, 88, 2885.10.1021/ja00964a071Search in Google Scholar
[11] W. Kantlehner, R. Stieglitz, H. Hauber, E. Haug, C. Regele, J. Prakt. Chem. 2000, 342, 256.10.1002/(SICI)1521-3897(200003)342:3<256::AID-PRAC256>3.0.CO;2-GSearch in Google Scholar
[12] C. H. Jutz, E. Müller, Angew. Chem., Int. Ed. Engl. 1966, 5, 724.10.1002/anie.196607241Search in Google Scholar
[13] W. Kantlehner, F. Wagner, H. Bredereck, Liebigs Ann. Chem. 1980, 344.10.1002/jlac.198019800303Search in Google Scholar
[14] W. Schroth, U. Jahn, D. Ströhl, Chem. Ber. 1994, 127, 2013.10.1002/cber.19941271026Search in Google Scholar
[15] U. Jahn, J. Anderlich, W. Schroth, Synthesis1997, 29, 573.10.1055/s-1997-1221Search in Google Scholar
[16] Z. Arnold, Collect. Czech. Chem. Commun. 1961, 26, 3051.10.1135/cccc19613051Search in Google Scholar
[17] B. Tinant, J.-P. Declercq, D. Bonvy, Z. Janousek, H. G. Viehe, J. Chem. Soc. Perkin Trans1993, 911.10.1039/p29930000911Search in Google Scholar
[18] W. Kantlehner, M. Vettel, H. Lehmann, K. Edelmann, R. Stieglitz, J. Ivanov, Prak. Chem./Chemiker Ztg. 1998, 340, 408.10.1002/prac.19983400503Search in Google Scholar
[19] W. Kantlehner, E. Haug, R. Stieglitz, W. Frey, R. Kreß, J. Mezger, Z. Naturforsch. 2002, 57b, 399.10.1515/znb-2002-0406Search in Google Scholar
[20] W. Kantlehner, H.-J. Lehmann, K. Edelmann, J. Mezger, I. C. Ivanov, Appl. Catal., A2008, 336, 148.10.1016/j.apcata.2007.08.027Search in Google Scholar
[21] W. Kantlehner, P. Speh, H. Lehmann, H.-J. Bräuner, E. Haug, W. W. Mergen, Chemiker Ztg.1990, 114, 176.Search in Google Scholar
[22] H. Bredereck, G. Simchen, G. Beck, Liebigs Ann. Chem. 1972, 762, 62.10.1002/jlac.19727620107Search in Google Scholar
[23] R. W. Kaesler, E. L. Goff, J. Org. Chem. 1983, 48, 4399.10.1021/jo00171a053Search in Google Scholar
[24] W. Kantlehner, G. Simchen, J. Mezger, E. V. Stoyanov, R. Kreß, W. Frey, B. Sievers, Z. Naturforsch. 2005, 60b, 231.10.1515/znb-2005-0218Search in Google Scholar
[25] W. Kantlehner, W. W. Mergen, E. Haug, Liebigs Ann. Chem. 1983, 290.10.1002/jlac.198319830214Search in Google Scholar
[26] G. Simchen, H. Hoffmann, H. Bredereck, Chem. Ber.1968, 191, 51.10.1002/cber.19681010109Search in Google Scholar
[27] W. Kantlehner, W. W. Mergen, E. Haug, P. Speh, J. Kapassakalidis, H.-J. Bräuner, Liebigs Ann. Chem. 1985, 1904.10.1002/jlac.198519850908Search in Google Scholar
[28] H. Bredereck, K. Bredereck, Chem. Ber.1961, 94, 2278.10.1002/cber.19610940853Search in Google Scholar
[29] W. Kantlehner, U. Greiner, Liebigs Ann. Chem. 1990, 965.10.1002/jlac.1990199001177Search in Google Scholar
©2018 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- In this Issue
- Preface
- The role of iminium salts, imines and related compounds in chemistry
- Original Articles
- A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines
- Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena
- Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
- Synthesis of functionalized pyrazole derivatives by regioselective [3+2] cycloadditions of N-Boc-α-amino acid-derived ynones
- Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines
- Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
- Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
- Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction
- Review
- Iminiumsalz-Strukturen bei der durch Pyridoxalphosphat (Vitamin B6) katalysierten Bildung von Aromastoffen und Fehlaromen im Wein
Articles in the same Issue
- Frontmatter
- In this Issue
- Preface
- The role of iminium salts, imines and related compounds in chemistry
- Original Articles
- A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines
- Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena
- Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
- Synthesis of functionalized pyrazole derivatives by regioselective [3+2] cycloadditions of N-Boc-α-amino acid-derived ynones
- Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines
- Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
- Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
- Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction
- Review
- Iminiumsalz-Strukturen bei der durch Pyridoxalphosphat (Vitamin B6) katalysierten Bildung von Aromastoffen und Fehlaromen im Wein
